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635-46-1 Usage

Uses

1,2,3,4-Tetrahydroquinoline is a reagent used in the synthesis of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamides displaying fungicidal activity.

Definition

ChEBI: A member of the class of quinolines that is the 1,2,3,4-tetrahydro derivative of quinoline.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 3905, 1986 DOI: 10.1248/cpb.34.3905Tetrahedron, 52, p. 1631, 1996 DOI: 10.1016/0040-4020(95)00991-4

Check Digit Verification of cas no

The CAS Registry Mumber 635-46-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 5 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 635-46:
(5*6)+(4*3)+(3*5)+(2*4)+(1*6)=71
71 % 10 = 1
So 635-46-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2

635-46-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (B22750)  1,2,3,4-Tetrahydroquinoline, 99%   

  • 635-46-1

  • 100g

  • 324.0CNY

  • Detail
  • Alfa Aesar

  • (B22750)  1,2,3,4-Tetrahydroquinoline, 99%   

  • 635-46-1

  • 500g

  • 1278.0CNY

  • Detail
  • Sigma-Aldrich

  • (87350)  1,2,3,4-Tetrahydroquinoline  purum, ≥96.0% (GC)

  • 635-46-1

  • 87350-100ML

  • 739.44CNY

  • Detail
  • Sigma-Aldrich

  • (87350)  1,2,3,4-Tetrahydroquinoline  purum, ≥96.0% (GC)

  • 635-46-1

  • 87350-500ML

  • 2,378.61CNY

  • Detail
  • Aldrich

  • (T15504)  1,2,3,4-Tetrahydroquinoline  98%

  • 635-46-1

  • T15504-5G

  • 230.49CNY

  • Detail
  • Aldrich

  • (T15504)  1,2,3,4-Tetrahydroquinoline  98%

  • 635-46-1

  • T15504-100G

  • 581.49CNY

  • Detail
  • Aldrich

  • (T15504)  1,2,3,4-Tetrahydroquinoline  98%

  • 635-46-1

  • T15504-500G

  • 1,499.94CNY

  • Detail

635-46-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2,3,4-tetrahydroquinoline

1.2 Other means of identification

Product number -
Other names Kusol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:635-46-1 SDS

635-46-1Synthetic route

quinoline
91-22-5

quinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With hydrogen; Wilkinson's catalyst In benzene at 85℃; under 16031.6 Torr; for 60h;100%
With hydrogen; polymer incarcerated palladium In tetrahydrofuran at 20℃; for 24h;100%
With hydrogen; Pd-containing polymer micelles In tetrahydrofuran at 20℃; under 760 Torr; for 24h;100%
3,4-dihydro-2H-quinoline-1-carbaldehyde
2739-16-4

3,4-dihydro-2H-quinoline-1-carbaldehyde

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water99%
With sodium hydroxide In ethanol for 6h; Hydrolysis; Heating;93%
With hydrogenchloride
1-(4-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline
182565-33-9

1-(4-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With potassium carbonate; thiophenol In acetonitrile for 24h;99%
3,4-dihydro-2H-quinoline-1-carboxylic acid allyl ester

3,4-dihydro-2H-quinoline-1-carboxylic acid allyl ester

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 24h;99%
Multi-step reaction with 2 steps
1: aminomethyl resin-supported N-propylbarbituric acid / Pd(PPh3)4 / tetrahydrofuran / 1 h / 20 - 40 °C
2: 86 percent / aminomethyl resin-supported N-propylbarbituric acid / Pd(PPh3)4 / tetrahydrofuran / 40 °C
View Scheme
C13H13NO2

C13H13NO2

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h;99%
5-bromoquinoline
4964-71-0

5-bromoquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With hydrogen In water at 20℃; for 24h; regioselective reaction;97%
2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

ethanol
64-17-5

ethanol

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With layered double hydroxide supported NiAl at 20 - 125℃; for 24h; Reagent/catalyst;97%
3,4-dihydro-2(1H)-quinolone
553-03-7

3,4-dihydro-2(1H)-quinolone

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate In toluene; butan-1-ol at 120℃; under 22502.3 Torr; for 6h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique; Autoclave;96%
With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 16h;90%
With tetra(n-butyl)ammonium borohydride In dichloromethane for 10h; Heating;86%
3-(2-chlorophenyl)-1-propanamine
18655-48-6

3-(2-chlorophenyl)-1-propanamine

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); sodium t-butanolate; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride In 1,4-dioxane at 100℃; for 4h;96%
With sodium hydride; tert-butyl alcohol; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride; palladium diacetate In 1,4-dioxane for 3h;
2-aminoquinoline
580-22-3

2-aminoquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With iridium(IV) oxide tetrahydrate; hydrogen In methanol at 20℃; for 24h; regioselective reaction;96%
1-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline
5434-99-1

1-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With magnesium; lithium tert-butoxide In tetrahydrofuran at 20℃; for 12h; Product distribution; Further Variations:; Reagents;94%
1,2,3,4-tetrahydroquinolinetrimethylmethanesulfonamide

1,2,3,4-tetrahydroquinolinetrimethylmethanesulfonamide

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; methoxybenzene In dichloromethane at 0℃; desulfonation;93%
1-(mesitylsulfonyl)-1,2,3,4-tetrahydroquinoline
326899-59-6

1-(mesitylsulfonyl)-1,2,3,4-tetrahydroquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;93%
1-acetyl-1,2,3,4-tetrahydroquinoline
4169-19-1

1-acetyl-1,2,3,4-tetrahydroquinoline

A

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

B

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With hydrogen In toluene at 160℃; under 45004.5 Torr; for 15h; Catalytic behavior; Autoclave;A 93%
B 89 %Chromat.
With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 18h; Autoclave;A 99 %Chromat.
B 99 %Chromat.
With C16H25MnN3O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In cyclohexane at 100℃; under 22502.3 Torr; for 16h; Inert atmosphere; Autoclave;A 88 %Chromat.
B 85 %Chromat.
quinoline
91-22-5

quinoline

4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

A

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

B

1-(4-(trifluoromethyl)benzyl)-1,2,3,4-tetrahydroquinoline
1611478-22-8

1-(4-(trifluoromethyl)benzyl)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (meta-(trifluoromethyl)phenyl)boronic acid In 1,2-dichloro-ethane at 60℃; for 12h; Kinetics; Reagent/catalyst;A n/a
B 93%
quinoline
91-22-5

quinoline

A

5,6,7,8-tetrahydroquinoline
10500-57-9

5,6,7,8-tetrahydroquinoline

B

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 150℃; under 38002.6 Torr; for 0.7h; Time; Concentration; Pressure;A 7%
B 92%
With hydrogen; platinum(IV) oxide In trifluoroacetic acidA 80%
B 6%
With Cp*Rh(2-(2-pyridyl)phenyl)H; hydrogen In tetrahydrofuran at 80℃; under 3040.2 Torr; for 48h; Catalytic behavior; Glovebox;A 58%
B 14%
N-(trichloroethoxy carbonyl)-tetrahydroquinoline

N-(trichloroethoxy carbonyl)-tetrahydroquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran; water for 0.75h;92%
3,4-dihydro-2H-quinoline-1-carboxylic acid allyl ester

3,4-dihydro-2H-quinoline-1-carboxylic acid allyl ester

A

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

B

1-allyl-1,2,3,4-tetrahydroquinoline
80574-15-8

1-allyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20 - 40℃; for 1h;A 92%
B n/a
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Stage #1: indan-1-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With sodium fluoride In hexane; dichloromethane; water at 0℃; for 0.5h;
92%
Stage #1: indan-1-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With water; sodium fluoride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; regioselective reaction;
92%
With dichloroaluminum hydride In cyclopentyl methyl ether at 0 - 20℃;69%
Multi-step reaction with 2 steps
1.1: hydrogenchloride; sodium cyanoborohydride / methanol / 0 - 20 °C
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.5 h / 0 °C / Inert atmosphere
2.2: 0.5 h / 0 °C / Inert atmosphere
View Scheme
Quinoline N-oxide
1613-37-2

Quinoline N-oxide

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Stage #1: Quinoline N-oxide With H2SiEt2; tris(pentafluorophenyl)borate In chloroform at 65℃; for 12h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h;
91%
With ammonium formate; 10percent palladium on carbon In methanol at 20℃; for 16h;87%
With hydrogen In toluene at 120℃; under 15001.5 Torr; for 48h; Autoclave;90 %Chromat.
With hydrogen In water; isopropyl alcohol Heating; High pressure; chemoselective reaction;68 %Chromat.
3-(2-aminophenyl)-1-propanol
57591-47-6

3-(2-aminophenyl)-1-propanol

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With C36H35IrN2P(1+)*C32H12BF24(1-); potassium tert-butylate In diethylene glycol dimethyl ether at 60℃; for 24h; Inert atmosphere;91%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium carbonate In toluene at 111℃; for 17h;96 % Chromat.
quinoline
91-22-5

quinoline

formic acid
64-18-6

formic acid

A

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

B

3,4-dihydro-2H-quinoline-1-carbaldehyde
2739-16-4

3,4-dihydro-2H-quinoline-1-carbaldehyde

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 130℃; for 0.166667h; Reagent/catalyst;A 91%
B 7%
With triethylamine In N,N-dimethyl-formamide at 130℃; for 2h; chemoselective reaction;
1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline
24310-24-5

1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With naphthalene; tetraethylammonium bromide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Electrolysis;90%
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;79%
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 8h; Inert atmosphere;32%
1-indanone O-(tert-butyldimethylsilyl)oxime
251980-46-8

1-indanone O-(tert-butyldimethylsilyl)oxime

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With borane-THF at 60℃; Reduction;88%
With dimethylsulfide borane complex; boron trifluoride diethyl etherate at 20℃;
quinoline
91-22-5

quinoline

isopropyl alcohol
67-63-0

isopropyl alcohol

A

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

B

1-(1-methylethyl)-1,2,3,4-tetrahydroquinoline
21863-25-2

1-(1-methylethyl)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With palladium 10% on activated carbon; zinc at 150℃; for 24h; Autoclave;A 88%
B 11%
With perchloric acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In water for 17h; Heating;A 69 % Chromat.
B n/a
3-Iodoquinoline
79476-07-6

3-Iodoquinoline

A

quinoline
91-22-5

quinoline

B

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With 2,6-dimethylpyridine; phenylsilane; indium(III) acetate In ethanol at 20℃; for 120h;A 88%
B 8%
With 2,6-dimethylpyridine; phenylsilane; indium(III) acetate In ethanol at 20℃; for 48h;A 29%
B 48%
1-(2-nitrobenzyl)-1,2,3,4-tetrahydroquinoline
198218-85-8

1-(2-nitrobenzyl)-1,2,3,4-tetrahydroquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With hydrazine In 1,4-dioxane; water for 0.333333h; Inert atmosphere; UV-irradiation;88%
N-nitroso-1,2,3,4-tetrahydroquinoline
5825-44-5

N-nitroso-1,2,3,4-tetrahydroquinoline

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;87%
1,3,4,5-tetrahydrobenzo<1,2-c>thiazepine 2,2-dioxide
80639-72-1

1,3,4,5-tetrahydrobenzo<1,2-c>thiazepine 2,2-dioxide

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
at 650℃; under 0.005 Torr;86.9%
at 650℃; under 0.005 Torr; Mechanism; flash vacuum pyrolyses (flow system);86.9%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

bromocyane
506-68-3

bromocyane

N-cyano-tetrahydro quinoline
1530-84-3

N-cyano-tetrahydro quinoline

Conditions
ConditionsYield
100%
With benzene
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-3(5H)-one
57369-31-0

1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-3(5H)-one

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; 2-chloropropionyl chloride In acetone for 1h; Inert atmosphere; Reflux;
Stage #2: With aluminum (III) chloride; sodium chloride at 150℃; for 1h; Inert atmosphere;
100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline; 2-chloropropionyl chloride In acetone for 1h; Reflux;
Stage #2: With aluminum (III) chloride; sodium chloride at 150℃; for 0.5h;
88%
With acetone Erhitzen des Reaktionsprodukts mit Aluminiumchlorid;
With aluminium trichloride 1.) acetone, reflux, 2 h, 2.) heating; Multistep reaction;
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

carbon dioxide
124-38-9

carbon dioxide

1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt
121565-21-7

1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 2h;
Stage #2: carbon dioxide In diethyl ether; hexane at -78℃;
100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether at -78 - 20℃; Cooling with acetone-dry ice; Inert atmosphere;
Stage #2: carbon dioxide In diethyl ether at -78℃; Cooling with ethanol-dry ice;
100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether at -78℃; for 17h; Schlenk technique; Inert atmosphere;
Stage #2: carbon dioxide In diethyl ether at -78 - 20℃; Schlenk technique;
100%
With n-butyllithium 1) THF, hexane, -78 deg C, 2) room temp.; Multistep reaction;
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In hexane; tert-butyl methyl ether at -20 - 20℃; Schlenk technique;
Stage #2: carbon dioxide In tetrahydrofuran; diethyl ether; hexane; tert-butyl methyl ether at -78 - 20℃; Schlenk technique;
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

1-(3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone
79066-90-3

1-(3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 20℃; for 5h;100%
With triethylamine In diethyl ether at 20℃; for 5h;100%
With triethylamine In diethyl ether at 0 - 20℃;98%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

N-nitroso-1,2,3,4-tetrahydroquinoline
5825-44-5

N-nitroso-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With sulfuric acid; sodium chloride; sodium nitrite In dichloromethane100%
With sulfuric acid; sodium nitrite In dichloromethane for 1.5h;100%
With sodium nitrite In water; acetic acid; ethyl acetate96%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

benzonitrile
100-47-0

benzonitrile

phenyl(1,2,3,4-tetrahydroquinolin-8-yl)methanone
28748-92-7

phenyl(1,2,3,4-tetrahydroquinolin-8-yl)methanone

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; benzonitrile With aluminum (III) chloride; water; boron trichloride In dichloromethane; toluene at 110℃;
Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 80℃; for 1h;
100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline; benzonitrile With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 110℃;
Stage #2: With hydrogenchloride; water at 80℃; for 1h;
100%
With aluminium trichloride; boron trichloride In 1,2-dichloro-ethane Acylation;
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline
5434-99-1

1-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With pyridine at 20℃; for 1h;100%
With pyridine at 50℃; Inert atmosphere;97%
With pyridine at 60 - 80℃; Inert atmosphere;87%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

1-(1H-imidazol-1-ylcarbonothioyl)-1,2,3,4-tetrahydroquinoline

1-(1H-imidazol-1-ylcarbonothioyl)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;100%
diethyl (piperidin-1-yl)ethynephosphonate

diethyl (piperidin-1-yl)ethynephosphonate

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

diethyl (E)-2-(piperidin-1-yl)-2-(1,2,3,4-tetrahydroquinolin-1-yl)ethenephosphonate

diethyl (E)-2-(piperidin-1-yl)-2-(1,2,3,4-tetrahydroquinolin-1-yl)ethenephosphonate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrachloromethane at 60℃;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

2-chloroacetylenephosphonic acid dimethyl ester
19519-59-6

2-chloroacetylenephosphonic acid dimethyl ester

dimethyl (1,2,3,4-tetrahydroqunolyl)ethynylphosphonate
1105013-11-3

dimethyl (1,2,3,4-tetrahydroqunolyl)ethynylphosphonate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 2h; Heating;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

carbon dioxide
124-38-9

carbon dioxide

1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt
121565-21-7

1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; n-butyllithium In diethyl ether at -78 - 20℃; for 2h; Cooling with acetone-dry ice;
Stage #2: carbon dioxide In diethyl ether at -78 - 20℃; Cooling with acetone-dry ice;
100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

4-carbethoxypiperidine
1126-09-6

4-carbethoxypiperidine

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate
1000211-89-1

ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; trichloromethyl chloroformate With triethylamine In dichloromethane
Stage #2: 4-carbethoxypiperidine In dichloromethane
100%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

1-(3-phenylpropyl)-1,2,3,4-tetrahydroquinoline

1-(3-phenylpropyl)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 2-methyltetrahydrofuran at 18℃; for 1h; Solvent; Reagent/catalyst; Green chemistry;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

α-bromopropionyl bromide
563-76-8

α-bromopropionyl bromide

2-bromo-1-(3,4-dihydroquinolin-1(2H)-yl)propan-1-one
118484-79-0

2-bromo-1-(3,4-dihydroquinolin-1(2H)-yl)propan-1-one

Conditions
ConditionsYield
With pyridine In dichloromethane at -78 - 20℃; for 1.75h;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

methyl 6-bromohexanoate
14273-90-6

methyl 6-bromohexanoate

N-methoxycarbonylpentyl-1,2,3,4-tetrahydroquinoline

N-methoxycarbonylpentyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 21h; Inert atmosphere;100%
With potassium carbonate; potassium iodide In acetonitrile for 38h; Inert atmosphere; Reflux;91%
With sodium carbonate; sodium iodide In acetonitrile for 48h; Reflux; Inert atmosphere;81%
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 30h; Inert atmosphere;76%
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 30h; Inert atmosphere;76%
furfural
98-01-1

furfural

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

trans-4,5-bis(dihydroquinoline)cyclopent-2-enone

trans-4,5-bis(dihydroquinoline)cyclopent-2-enone

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0166667h;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

isopentyl nitrite
110-46-3

isopentyl nitrite

N-nitroso-1,2,3,4-tetrahydroquinoline
5825-44-5

N-nitroso-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With 4-(1,1-dimethylethyl)benzoic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

carbon dioxide
124-38-9

carbon dioxide

C10H10NO2(1-)*Li(1+)

C10H10NO2(1-)*Li(1+)

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline In diethyl ether at -78℃; for 0.5h; Schlenk technique;
Stage #2: With n-butyllithium In diethyl ether for 2h; Inert atmosphere;
Stage #3: carbon dioxide In diethyl ether at -78 - 20℃;
100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

carbon dioxide
124-38-9

carbon dioxide

C9H11N*2Li(1+)*CO3(2-)

C9H11N*2Li(1+)*CO3(2-)

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether at -78℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: carbon dioxide In diethyl ether at -78℃; Schlenk technique; Inert atmosphere;
100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

lithium 1,2,3,4-tetrahydroquinolide
33735-01-2

lithium 1,2,3,4-tetrahydroquinolide

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline In diethyl ether at -78℃; for 0.5h; Schlenk technique; Cooling with acetone-dry ice;
Stage #2: With n-butyllithium In diethyl ether for 2h; Inert atmosphere;
100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride

1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride

C20H19N3O

C20H19N3O

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 0.5h;99.7%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

formic acid
64-18-6

formic acid

3,4-dihydro-2H-quinoline-1-carbaldehyde
2739-16-4

3,4-dihydro-2H-quinoline-1-carbaldehyde

Conditions
ConditionsYield
Stage #1: formic acid With acetic anhydride at 70℃; for 1h; Inert atmosphere;
Stage #2: 1,2,3,4-tetrahydroisoquinoline at 50℃; Inert atmosphere;
99%
With iodine at 70℃;96%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

quinoline
91-22-5

quinoline

Conditions
ConditionsYield
With oxygen In para-xylene at 110℃; for 3.5h;99%
With pyridine at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Irradiation;99%
With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide In tert-Amyl alcohol at 95℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;99%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

2-[2-(p-tolylsulfanyl)phenyl]acetic acid
16174-75-7

2-[2-(p-tolylsulfanyl)phenyl]acetic acid

1-(3,4-Dihydro-2H-quinolin-1-yl)-2-(2-p-tolylsulfanyl-phenyl)-ethanone
207349-81-3

1-(3,4-Dihydro-2H-quinolin-1-yl)-2-(2-p-tolylsulfanyl-phenyl)-ethanone

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In benzene for 2h; Ambient temperature;99%
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

1-[(2E)-3-phenylprop-2-en-1-yl]-1,2,3,4-tetrahydroquinoline

1-[(2E)-3-phenylprop-2-en-1-yl]-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With benzoic acid; DavePhos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 50℃;99%
With chlorobis(cyclooctene)rhodium(I) dimer; 1,3-bis-(diphenylphosphino)propane; benzene-1,2-dicarboxylic acid In tetrahydrofuran at 70℃; for 18h; Glovebox; enantioselective reaction;99%
With tetrakis(triphenylphosphine) palladium(0); benzoic acid; CyJohnPhos In water at 100℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction;98%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

methyl chloroformate
79-22-1

methyl chloroformate

3,4-dihydro-2H-quinoline-1-carboxylic acid methyl ester
94567-78-9

3,4-dihydro-2H-quinoline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 50℃; for 6h;99%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; Cooling with ice; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5.16667h; Cooling with ice;

635-46-1Relevant articles and documents

Correction to: Halogen-Bonding-Induced Hydrogen Transfer to C=N Bond with Hantzsch Ester (Org. Lett. (2014) 16:12 (3244-3247) DOI: 10.1021/ol501259q)

He, Wei,Ge, Yi-Cen,Tan, Choon-Hong

, p. 7684 - 7684 (2019)

The structure of C1 has been revised in the Graphical Abstract/Table of Contents graphic.(Figure presented)

Study of Hydrodesulfurization by the Use of 35S-Labeled Dibenzothiophene. 2. Behavior of Sulfur in HDS, HDO, and HDN on Sulfided Mo/Al2O3 Catalyst

Kabe, Toshiaki,Quian, Weihua,Ishihara, Atsushi

, p. 912 - 916 (1994)

To investigate the behavior of sulfur during the hydrodesulfurization (HDS), 35S-labeled dibenzothiophene (DBT) was reacted on sulfided Mo/Al2O3.It was found that 35S in DBT was accommodated on the catalyst and the concentration of 35S on the catalyst always reached a steady state under fixed reaction conditions. 35S accommodated on the catalyst cannot be removed without the incorporation of sulfur from HDS of sulfur compounds such as DBT, benzothiophene, thiophene, and thiophenol.The removal rate of 35S from the catelyst depended upon the rate of HDS of these compounds, that is, the amount of sulfur incorporated into the catalyst.It was suggested that H2S is formed from some portion of sulfur on the surface of the catalyst othe than from that in the sulfur compounds.When hydrodenitrogenation (HDN) and hydrodeoxygenation (HDO) reactions were carried out on the catalyst containing 35S, some portion of 35S could be replaced by oxygen atoms and released as H2S; in contrast to this, 35S was hardly replaced by N atoms.

Chemoselective and Tandem Reduction of Arenes Using a Metal–Organic Framework-Supported Single-Site Cobalt Catalyst

Antil, Neha,Kumar, Ajay,Akhtar, Naved,Begum, Wahida,Chauhan, Manav,Newar, Rajashree,Rawat, Manhar Singh,Manna, Kuntal

supporting information, p. 1031 - 1040 (2022/01/19)

The development of heterogeneous, chemoselective, and tandem catalytic systems using abundant metals is vital for the sustainable synthesis of fine and commodity chemicals. We report a robust and recyclable single-site cobalt-hydride catalyst based on a porous aluminum metal–organic framework (DUT-5 MOF) for chemoselective hydrogenation of arenes. The DUT-5 node-supported cobalt(II) hydride (DUT-5-CoH) is a versatile solid catalyst for chemoselective hydrogenation of a range of nonpolar and polar arenes, including heteroarenes such as pyridines, quinolines, isoquinolines, indoles, and furans to afford cycloalkanes and saturated heterocycles in excellent yields. DUT-5-CoH exhibited excellent functional group tolerance and could be reusable at least five times without decreased activity. The same MOF-Co catalyst was also efficient for tandem hydrogenation–hydrodeoxygenation of aryl carbonyl compounds, including biomass-derived platform molecules such as furfural and hydroxymethylfurfural to cycloalkanes. In the case of hydrogenation of cumene, our spectroscopic, kinetic, and density functional theory (DFT) studies suggest the insertion of a trisubstituted alkene intermediate into the Co–H bond occurring in the turnover limiting step. Our work highlights the potential of MOF-supported single-site base–metal catalysts for sustainable and environment-friendly industrial production of chemicals and biofuels.

Ru-decorated N-doped carbon nanoflakes for selective hydrogenation of levulinic acid to γ-valerolactone and quinoline to tetrahydroquinoline with HCOOH in water

Chauhan, Arzoo,Kar, Ashish Kumar,Srivastava, Rajendra

, (2022/03/27)

The effective dissociation of biomass-derived formic acid, as a sustainable hydrogen source, in water is explored for the hydrogenation of levulinic acid (LA) and quinoline. Ru decorated carbon nanoflakes prepared by carboreduction (in Ar/H2 atmosphere) of Ru containing N-doped carbon were used as catalysts. The successful formation of Ru-decorated N-doped carbons was confirmed by numerous spectroscopic tools. The catalyst exhibited outstanding activity and selectivity for the hydrogenation of LA and quinoline using formic acid as a hydrogen donor in water under mild conditions. The catalyst afforded 99.8% LA conversion and 100% selectivity for γ-valerolactone (GVL), whereas 99.8% quinoline conversion and 93% selectivity for 1,2,3,4-tetrahydroquinoline (THQ) were obtained. Recycling experiments suggested that the catalyst was stable even after the 5 cycles. Various controlled experiments and characterizations were conducted to demonstrate the structure-activity relations and suggest plausible reaction mechanisms for the hydrogenation of LA and quinoline. The exploration of formic acid as a sustainable H2 source and the development of metal decorated N-doped carbons for hydrogenation of LA and quinoline will be fascinating to catalysis researchers and industrialists.

Heterogeneous Hydrogenation of Quinoline Derivatives Effected by a Granular Cobalt Catalyst

Timelthaler, Daniel,Topf, Christoph

, (2021/11/22)

We communicate a convenient method for the pressure hydrogenation of quinolines in aqueous solution by using a particulate cobalt-based catalyst that is prepared in situ from simple Co(OAc)2 4H2O through reduction with abundant zinc powder. This catalytic protocol permits a brisk and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines thereby relying solely on easy-to-handle reagents that are all readily obtained from commercial sources. Both the reaction setup assembly and the autoclave charging procedure are conducted on the bench outside an inert-gas-operated containment system, thus rendering the overall synthesis time-saving and operationally very simple.

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