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613-50-3

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613-50-3 Usage

Chemical Properties

beige to light brown powder

Check Digit Verification of cas no

The CAS Registry Mumber 613-50-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 3 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 613-50:
(5*6)+(4*1)+(3*3)+(2*5)+(1*0)=53
53 % 10 = 3
So 613-50-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H6N2O2/c12-11(13)8-3-4-9-7(6-8)2-1-5-10-9/h1-6H

613-50-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A17212)  6-Nitroquinoline, 98+%   

  • 613-50-3

  • 5g

  • 421.0CNY

  • Detail
  • Alfa Aesar

  • (A17212)  6-Nitroquinoline, 98+%   

  • 613-50-3

  • 10g

  • 446.0CNY

  • Detail
  • Alfa Aesar

  • (A17212)  6-Nitroquinoline, 98+%   

  • 613-50-3

  • 50g

  • 1778.0CNY

  • Detail
  • Aldrich

  • (N24005)  6-Nitroquinoline  98%

  • 613-50-3

  • N24005-25G

  • 1,007.72CNY

  • Detail

613-50-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Nitroquinoline

1.2 Other means of identification

Product number -
Other names Quinoline, 6-nitro-

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:613-50-3 SDS

613-50-3Synthetic route

6-chloroquinoline
612-57-7

6-chloroquinoline

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With Tris(3,6-dioxaheptyl)amine; sodium nitrite; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos In tert-butyl alcohol at 130℃; for 24h; Product distribution / selectivity; Inert atmosphere;97%
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite In tert-butyl alcohol at 130℃; for 24h; regioselective reaction;97%
quinolin-6-yl triflate
173089-80-0

quinolin-6-yl triflate

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With Tris(3,6-dioxaheptyl)amine; sodium nitrite; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos In tert-butyl alcohol at 130℃; for 24h; Product distribution / selectivity; Inert atmosphere;94%
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite In tert-butyl alcohol at 130℃; for 24h; regioselective reaction;94%
6-nitro-1,2,3,4-tetrahydroquinoline
14026-45-0

6-nitro-1,2,3,4-tetrahydroquinoline

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With perylene diimide covalent immobilized to SiO2 nanospheres; air In N,N-dimethyl acetamide at 20℃; UV-irradiation;91%
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In acetonitrile at 100℃; under 11251.1 Torr; for 24h; Autoclave;89%
With hexagonal boron carbon nitride In water at 25℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation;89%
6-bromoquinoline
5332-25-2

6-bromoquinoline

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With potassium nitrite; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 130℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;82%
With potassium nitrite; basolite C300 In dimethyl sulfoxide at 130℃; for 48h; Inert atmosphere;78%
6-nitroquinoline-N-oxide
13675-92-8

6-nitroquinoline-N-oxide

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Irradiation; chemoselective reaction;73%
4-nitro-N-2-propynylbenzenamine
75077-46-2

4-nitro-N-2-propynylbenzenamine

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 70℃; for 72h; Sealed tube;57%
4-nitro-aniline
100-01-6

4-nitro-aniline

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With arsenic(III) trioxide Skraup reaction;47%
4-nitro-aniline
100-01-6

4-nitro-aniline

glycerol
56-81-5

glycerol

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With sulfuric acid; iodine at 160 - 170℃; for 2h; Cycloaddition; Aromatization;18.3%
With sulfuric acid; nitrobenzene
With sulfuric acid; orthoarsenic acid
With sulfuric acid; vanadia; sodium 3-nitrobenzenesulfonate at 145℃;
With sulfuric acid In water at 36 - 200℃; for 0.25h; Microwave irradiation; Green chemistry;
6-azidoquinoline
20377-02-0

6-azidoquinoline

A

6-nitroquinoline
613-50-3

6-nitroquinoline

B

3-nitrosoindolizine-8-carbaldehyde
1382859-30-4

3-nitrosoindolizine-8-carbaldehyde

C

C18H12N4O4
1382859-31-5

C18H12N4O4

Conditions
ConditionsYield
With oxygen In acetonitrile at 20℃; Irradiation;A 14%
B n/a
C n/a
With oxygen In acetonitrile at 19.84℃; Irradiation;A 14%
B n/a
C n/a
quinoline
91-22-5

quinoline

A

6-nitroquinoline
613-50-3

6-nitroquinoline

B

7-nitroquinoline
613-51-4

7-nitroquinoline

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; acetic acid und Natriumnitrit;
4-nitro-aniline
100-01-6

4-nitro-aniline

glycerol
56-81-5

glycerol

A

4,7-phenanthroline
230-07-9

4,7-phenanthroline

B

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With sulfuric acid; nitrobenzene
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

glycerol
56-81-5

glycerol

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With arsenic(V) oxide; sulfuric acid
6-nitro-quinoline-carboxylic acid-(4)-hydrochloride

6-nitro-quinoline-carboxylic acid-(4)-hydrochloride

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
durch Sublimation;
quinoloic acid

quinoloic acid

6-nitroquinoline
613-50-3

6-nitroquinoline

glycerol
56-81-5

glycerol

sodium-salt of/the/ 2-amino-5-nitro-benzenesulfonic acid

sodium-salt of/the/ 2-amino-5-nitro-benzenesulfonic acid

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With sulfuric acid; water; orthoarsenic acid
quinoline
91-22-5

quinoline

nitric acid
7697-37-2

nitric acid

acetic anhydride
108-24-7

acetic anhydride

A

8-nitroquinoline
607-35-2

8-nitroquinoline

B

3-nitroquinoline
17576-53-3

3-nitroquinoline

C

6-nitroquinoline
613-50-3

6-nitroquinoline

quinoline
91-22-5

quinoline

acetic anhydride
108-24-7

acetic anhydride

lithium nitrate

lithium nitrate

copper (I)-nitrate

copper (I)-nitrate

A

8-nitroquinoline
607-35-2

8-nitroquinoline

B

3-nitroquinoline
17576-53-3

3-nitroquinoline

C

6-nitroquinoline
613-50-3

6-nitroquinoline

sulfuric acid
7664-93-9

sulfuric acid

nitrobenzene
98-95-3

nitrobenzene

4-nitro-aniline
100-01-6

4-nitro-aniline

glycerol
56-81-5

glycerol

6-nitroquinoline
613-50-3

6-nitroquinoline

1-methanesulfonyl-6-nitro-1,2-dihydro-quinoline
333383-87-2

1-methanesulfonyl-6-nitro-1,2-dihydro-quinoline

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 80℃;
N-(4-nitrophenyl)methanesulfonamide
5825-62-7

N-(4-nitrophenyl)methanesulfonamide

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / methanol
2: 16 percent / TfOH / CH2Cl2 / 2 h / 0 °C
3: KOH / dimethylsulfoxide / 80 °C
View Scheme
4-nitro-aniline
100-01-6

4-nitro-aniline

resin-O-CO-NH-C(NH)-1H-pyrazole

resin-O-CO-NH-C(NH)-1H-pyrazole

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / CH2Cl2 / 20 °C
2: Et3N / methanol
3: 16 percent / TfOH / CH2Cl2 / 2 h / 0 °C
4: KOH / dimethylsulfoxide / 80 °C
View Scheme
N-(4-nitro-phenyl)-N-(3-oxo-propyl)-methanesulfonamide
333383-74-7

N-(4-nitro-phenyl)-N-(3-oxo-propyl)-methanesulfonamide

6-nitroquinoline
613-50-3

6-nitroquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 16 percent / TfOH / CH2Cl2 / 2 h / 0 °C
2: KOH / dimethylsulfoxide / 80 °C
View Scheme
6-nitroquinoline-borane
102941-79-7

6-nitroquinoline-borane

A

6-nitroquinoline
613-50-3

6-nitroquinoline

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water In 1,4-dioxane; water Kinetics; byproducts: H2; hydrolysis of the amine-borane in an aq. dioxane soln. at 25°C;
6-nitroquinoline
613-50-3

6-nitroquinoline

6-aminoquinoline
580-15-4

6-aminoquinoline

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;100%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; for 2h;100%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry;99%
6-nitroquinoline
613-50-3

6-nitroquinoline

Tetrahydro-furan; compound with trifluoroborane

Tetrahydro-furan; compound with trifluoroborane

6-nitroquinoline-borane
102941-79-7

6-nitroquinoline-borane

Conditions
ConditionsYield
In tetrahydrofuran stirring a mixt. of 4-chloroquinoline and BF3*THF in dry THF at 0°C under N2; isolation of the amine-borane from the reaction mixt. by removal of thesolvent;100%
6-nitroquinoline
613-50-3

6-nitroquinoline

5-amino-6-nitroquinoline
35975-00-9

5-amino-6-nitroquinoline

Conditions
ConditionsYield
With N,N-tetramethylene-thiocarbamoyl-sulphenamide98%
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide at 20℃; for 1h;95%
With hydroxylamine hydrochloride94%
formic acid
64-18-6

formic acid

6-nitroquinoline
613-50-3

6-nitroquinoline

N-(quinolin-6-yl)formamide
83407-37-8

N-(quinolin-6-yl)formamide

Conditions
ConditionsYield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 4h; Inert atmosphere; chemoselective reaction;96%
With cobalt nanoparticles coated by N,P-codoped carbon shell pyrolyzed at 800°C In tetrahydrofuran at 120℃; for 12h; Schlenk technique; Inert atmosphere;78%
6-nitroquinoline
613-50-3

6-nitroquinoline

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

Allyl chloroformate
2937-50-0

Allyl chloroformate

C24H32N2O4Si

C24H32N2O4Si

Conditions
ConditionsYield
Stage #1: tris-iso-propylsilyl acetylene With isopropylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran for 1h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 20℃; for 2h; Inert atmosphere;
Stage #3: 6-nitroquinoline; Allyl chloroformate Further stages;
96%
6-nitroquinoline
613-50-3

6-nitroquinoline

2-Diazo-3-oxo-butyric acid methyl ester
24762-04-7

2-Diazo-3-oxo-butyric acid methyl ester

benzyl chloroformate
501-53-1

benzyl chloroformate

methyl 2-diazo-4-[2-(6-nitro-1-benzyloxycarbonyl-1,2-dihydro)quinoline]-3-oxobutyrate

methyl 2-diazo-4-[2-(6-nitro-1-benzyloxycarbonyl-1,2-dihydro)quinoline]-3-oxobutyrate

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 5 - 8℃; for 1h;95%
6-nitroquinoline
613-50-3

6-nitroquinoline

6-nitro-1,2,3,4-tetrahydroquinoline
14026-45-0

6-nitro-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; water In water; isopropyl alcohol for 17h; Heating;94%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C38H52N4Se2(2+)*2CF3O3S(1-) In chloroform-d1 at 20℃; for 12h; Sealed tube;92%
With formic acid; sulfuric acid In water at 80℃; for 24h; pH=2.5; Schlenk technique; Inert atmosphere;91%
6-nitroquinoline
613-50-3

6-nitroquinoline

6-nitroquinoline-N-oxide
13675-92-8

6-nitroquinoline-N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform93%
With dihydrogen peroxide In water for 0.333333h; Sonication;88%
With fluorosulfonyl fluoride; dihydrogen peroxide; potassium carbonate In methanol at 23 - 32℃; Sealed tube;84.9%
6-nitroquinoline
613-50-3

6-nitroquinoline

1-chloro-N,N-dimethylmethane sulfonamide
35427-68-0

1-chloro-N,N-dimethylmethane sulfonamide

5-(Dimethylaminosulfonylmethyl)-6-nitroquinoline
105199-27-7

5-(Dimethylaminosulfonylmethyl)-6-nitroquinoline

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -30 - -25℃; for 0.25h;92%
6-nitroquinoline
613-50-3

6-nitroquinoline

1-(trimethylsilyl)-1-hexyne
3844-94-8

1-(trimethylsilyl)-1-hexyne

phenyl chloroformate
1885-14-9

phenyl chloroformate

2-Hex-1-ynyl-6-nitro-2H-quinoline-1-carboxylic acid phenyl ester

2-Hex-1-ynyl-6-nitro-2H-quinoline-1-carboxylic acid phenyl ester

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 83℃; for 4h;92%
6-nitroquinoline
613-50-3

6-nitroquinoline

3-iodo-6-nitroquinoline

3-iodo-6-nitroquinoline

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iodine In water; acetonitrile at 80℃; for 17h; regioselective reaction;91%
With tert.-butylhydroperoxide; iodine In 1,2-dichloro-ethane at 120℃; for 24h; regioselective reaction;69%
6-nitroquinoline
613-50-3

6-nitroquinoline

2,5-hexanedione
110-13-4

2,5-hexanedione

A

6-aminoquinoline
580-15-4

6-aminoquinoline

B

C15H14N2

C15H14N2

Conditions
ConditionsYield
With formic acid for 12h; Autoclave; Inert atmosphere; Green chemistry;A 8.3%
B 90.6%
6-nitroquinoline
613-50-3

6-nitroquinoline

1-Phenyl-2-(trimethylsilyl)acetylene
2170-06-1

1-Phenyl-2-(trimethylsilyl)acetylene

phenyl chloroformate
1885-14-9

phenyl chloroformate

6-Nitro-2-phenylethynyl-2H-quinoline-1-carboxylic acid phenyl ester

6-Nitro-2-phenylethynyl-2H-quinoline-1-carboxylic acid phenyl ester

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 83℃; for 4h;90%
6-nitroquinoline
613-50-3

6-nitroquinoline

2-chloro-propanoic acid, ethyl ester
535-13-7

2-chloro-propanoic acid, ethyl ester

ethyl 1,9b-dihydro-1-methylisoxazolo[4,3-f]quinoline-1-carboxylate 3-oxide

ethyl 1,9b-dihydro-1-methylisoxazolo[4,3-f]quinoline-1-carboxylate 3-oxide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 2h;90%
6-nitroquinoline
613-50-3

6-nitroquinoline

6-nitro-1,2-dihydroquinolin-2-one
64495-55-2

6-nitro-1,2-dihydroquinolin-2-one

Conditions
ConditionsYield
With water; chloroacetic acid ethyl ester In ethyl acetate for 0.5h; Microwave irradiation;89%
With xanthine oxidase from bovine milk; oxygen In aq. phosphate buffer; N,N-dimethyl-formamide at 40℃; for 72h; pH=7.4; Concentration; Reagent/catalyst; Enzymatic reaction;2%
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / chloroform / 20 °C
2: water; potassium carbonate; p-toluenesulfonyl chloride / chloroform / 20 °C
View Scheme
6-nitroquinoline
613-50-3

6-nitroquinoline

phenylboronic acid
98-80-6

phenylboronic acid

N-phenylquinolin-6-amine
70682-98-3

N-phenylquinolin-6-amine

Conditions
ConditionsYield
Stage #1: 6-nitroquinoline With [2,2]bipyridinyl; [MoO2Cl2(dmf)2] In toluene for 0.0333333h;
Stage #2: phenylboronic acid With triphenylphosphine In toluene at 100℃; for 14h;
87%
6-nitroquinoline
613-50-3

6-nitroquinoline

6-nitro-quinolin-5-ol
58416-46-9

6-nitro-quinolin-5-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium tert-butylate In ammonia at -33℃;86%
6-nitroquinoline
613-50-3

6-nitroquinoline

8-fluoro-6-nitroquinoline

8-fluoro-6-nitroquinoline

Conditions
ConditionsYield
With sulfuric acid; fluorine at 5℃;86%
With FlutecTM PP11; sulfuric acid; fluorine at 15℃;
6-nitroquinoline
613-50-3

6-nitroquinoline

3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

N-(quinolin-6-yl)benzo[d][1,3]dioxole-5-sulfonamide

N-(quinolin-6-yl)benzo[d][1,3]dioxole-5-sulfonamide

Conditions
ConditionsYield
With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;85%
With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere;85%
6-nitroquinoline
613-50-3

6-nitroquinoline

chloromethyl phenyl sulfone
7205-98-3

chloromethyl phenyl sulfone

6-Nitro-5-(phenylsulfonylmethyl)quinoline
105199-25-5

6-Nitro-5-(phenylsulfonylmethyl)quinoline

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h;83%
6-nitroquinoline
613-50-3

6-nitroquinoline

2-chloro-propionic acid methyl ester
17639-93-9

2-chloro-propionic acid methyl ester

methyl 1,9b-dihydro-1-methylisoxazolo[4,3-f]quinoline-1-carboxylate 3-oxide

methyl 1,9b-dihydro-1-methylisoxazolo[4,3-f]quinoline-1-carboxylate 3-oxide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 2h;83%
6-nitroquinoline
613-50-3

6-nitroquinoline

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-(quinolin-6-ylamino)naphthalene-1,4-dione

2-(quinolin-6-ylamino)naphthalene-1,4-dione

Conditions
ConditionsYield
In water at 20℃; for 5h;81%
With zinc(II) acetate dihydrate; acetic acid; zinc In water at 20℃; for 5h;51%
6-nitroquinoline
613-50-3

6-nitroquinoline

(4-chlorophenoxy)acetonitrile
3598-13-8

(4-chlorophenoxy)acetonitrile

(6-Nitro-5-quinolinyl)acetonitrile
105199-28-8

(6-Nitro-5-quinolinyl)acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -10℃; for 0.416667h;80%
6-nitroquinoline
613-50-3

6-nitroquinoline

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

(3aR*,9bS*)-2-benzyl-3a-nitro-2,3,3a,9b-tetrahydro-1H-pyrrolo[3,4-f]quinoline

(3aR*,9bS*)-2-benzyl-3a-nitro-2,3,3a,9b-tetrahydro-1H-pyrrolo[3,4-f]quinoline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;80%
6-nitroquinoline
613-50-3

6-nitroquinoline

5-styryl-4-nitro-3-methylisoxazole
53557-94-1

5-styryl-4-nitro-3-methylisoxazole

3-methyl-4-nitro-5-(3-(6-nitroquinolin-2-yl)-2-phenylpropyl)isoxazole

3-methyl-4-nitro-5-(3-(6-nitroquinolin-2-yl)-2-phenylpropyl)isoxazole

Conditions
ConditionsYield
In water at 120℃; for 15h; Inert atmosphere; Green chemistry;80%
6-nitroquinoline
613-50-3

6-nitroquinoline

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

1-methyl-6-nitroquinolinium triflate

1-methyl-6-nitroquinolinium triflate

Conditions
ConditionsYield
In benzene for 0.5h; Reflux;80%

613-50-3Relevant articles and documents

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material

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Paragraph 0010-0011; 0028-0029, (2021/06/26)

The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee

supporting information, p. 2876 - 2894 (2021/02/01)

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Metal–Organic Frameworks for the Exploitation of Distance between Active Sites in Efficient Photocatalysis

Deng, Hexiang,Gong, Xuan,Jiang, Zhuo,Lu, Lingxiang,Shu, Yufei,Wang, Chao,Xu, Xiaohui

supporting information, p. 5326 - 5331 (2020/02/18)

Discoveries of the accurate spatial arrangement of active sites in biological systems and cooperation between them for high catalytic efficiency are two major events in biology. However, precise tuning of these aspects is largely missing in the design of artificial catalysts. Here, a series of metal–organic frameworks (MOFs) were used, not only to overcome the limit of distance between active sites in bio-systems, but also to unveil the critical role of this distance for efficient catalysis. A linear correlation was established between photocatalytic activity and the reciprocal of inter active-site distance; a smaller distance led to higher activity. Vacancies created at selected crystallographic positions of MOFs promoted their photocatalytic efficiency. MOF-525-J33 with 15.6 ? inter active-site distance and 33 % vacancies exhibited unprecedented high turnover frequency of 29.5 h?1 in visible-light-driven acceptorless dehydrogenation of tetrahydroquinoline at room temperature.

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