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3418-45-9

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3418-45-9 Usage

General Description

3-Quinolinol, also known as 1,2,3,4-tetrahydroquinoline, is a chemical compound with a molecular formula C9H11NO. It is a colorless to pale yellow liquid with a faint odor, and it is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other fine chemicals. 3-Quinolinol has been studied for its potential use as an antimicrobial and antifungal agent, as well as its potential application in the treatment of neurodegenerative diseases. It is also used as a chelating agent in the extraction and purification of metals, and as a corrosion inhibitor in metalworking fluids. Additionally, 3-Quinolinol is considered a potential environmental hazard and has been subject to environmental risk assessments due to its potential toxicity to aquatic organisms.

Check Digit Verification of cas no

The CAS Registry Mumber 3418-45-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,1 and 8 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 3418-45:
(6*3)+(5*4)+(4*1)+(3*8)+(2*4)+(1*5)=79
79 % 10 = 9
So 3418-45-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-4,8,10-11H,5-6H2

3418-45-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2,3,4-Tetrahydro-3-quinolinol

1.2 Other means of identification

Product number -
Other names 1,2,3,4-Tetrahydro-9H-carbazole-9-carboxamide

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:3418-45-9 SDS

3418-45-9Synthetic route

quinoline
91-22-5

quinoline

A

1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

B

1,2,3,4-tetrahydroquinolin-2-ol

1,2,3,4-tetrahydroquinolin-2-ol

Conditions
ConditionsYield
Stage #1: quinoline With borane-THF; boron trichloride In hexane at 0 - 65℃; for 4h; Inert atmosphere;
Stage #2: With sodium perborate; water at 20℃; for 2h; Reagent/catalyst; Inert atmosphere;
A 70%
B 21%
3-hydroxyquinoline
580-18-7

3-hydroxyquinoline

1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
With ethanol; sodium at 80℃; for 2h;48%
With ethanol; palladium at 55℃; Hydrogenation;
With potassium hydroxide; water elektrochemische Reduktion;
With sulfuric acid; water elektrochemische Reduktion;
With ethanol; sodium
quinoline
91-22-5

quinoline

1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
Stage #1: quinoline With monochloroborane dimethyl sulfide complex In tetrahydrofuran at 0 - 65℃; for 48h; Inert atmosphere;
Stage #2: With sodium perborate; water at 20℃; for 2h; Reagent/catalyst; Inert atmosphere;
45%
Multi-step reaction with 2 steps
1: tris(pentafluorophenyl)borate / chloroform-d1 / 24 h / 25 °C / Inert atmosphere
2: sodium perborate tetrahydrate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: tris(pentafluorophenyl)borate / chloroform-d1 / 24 h / 85 °C / Inert atmosphere
2: sodium perborate tetrahydrate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
View Scheme
3-hydroxyquinoline
580-18-7

3-hydroxyquinoline

sulfuric acid
7664-93-9

sulfuric acid

water
7732-18-5

water

1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
bei der elektrochemischen Reduktion an Blei-Kathoden;
3-hydroxyquinoline
580-18-7

3-hydroxyquinoline

water
7732-18-5

water

KOH-solution

KOH-solution

1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
bei der elektrochemischen Reduktion an Nickel-Kathoden;
C21H17B2NO4

C21H17B2NO4

1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
With sodium perborate tetrahydrate In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere;
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-((tert-butyldimethylsilyl)oxy)-1,2,3,4-tetrahydroquinoline

3-((tert-butyldimethylsilyl)oxy)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With 1H-imidazole In tetrahydrofuran at 80℃; for 12h;38%
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

1-bromomethyl-3-trifluoromethylbenzene
402-23-3

1-bromomethyl-3-trifluoromethylbenzene

1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2H-quinolin-3-ol

1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2H-quinolin-3-ol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 25℃; for 12h;18.4%
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

1-(3-(3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

1-(3-(3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

1-(3-(6-bromo-3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

1-(3-(6-bromo-3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

1-(3-(3-((tert-butyldimethylsilyl)oxy)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

1-(3-(3-((tert-butyldimethylsilyl)oxy)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C
4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

(S)-1-[3-[3-hydroxy-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]ethanone

(S)-1-[3-[3-hydroxy-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]ethanone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C
4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

(S)-1-[3-[3-methoxy-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]ethanone

(S)-1-[3-[3-methoxy-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]ethanone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2.1: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
3.1: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C
4.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere
6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
6.2: 16 h / 0 - 25 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

1-(5-acetyl-1-((S)-tetrahydrofuran-3-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydroquinolin-3-yl methanesulfonate

1-(5-acetyl-1-((S)-tetrahydrofuran-3-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydroquinolin-3-yl methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C
4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere
6: triethylamine / dichloromethane / 2 h / 0 - 25 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

A

(S)-1-(5-acetyl-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinoline-3-carbonitrile

(S)-1-(5-acetyl-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinoline-3-carbonitrile

B

(S)-2-[1-(5-acetyl-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-5-(1-methylpyrazol-4-yl)indolin-2-yl]acetonitrile

(S)-2-[1-(5-acetyl-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-5-(1-methylpyrazol-4-yl)indolin-2-yl]acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C
2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C
4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere
6: triethylamine / dichloromethane / 2 h / 0 - 25 °C
7: dimethyl sulfoxide / 16 h / 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

6-bromo-1,2,3,4-tetrahydroquinolin-3-ol

6-bromo-1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 15h;
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

6-bromo-3-((tert-butyldimethylsilyl)oxy)-1,2,3,4-tetrahydroquinoline

6-bromo-3-((tert-butyldimethylsilyl)oxy)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

(6-bromo-3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

(6-bromo-3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

(6-bromo-3-hydroxy-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

(6-bromo-3-hydroxy-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
4: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

(6-bromo-3-fluoro-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

(6-bromo-3-fluoro-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
4: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C
5: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

tert-butyl 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)acetate

tert-butyl 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
4: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C
5: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C
6: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

tert-butyl 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)propanoate

tert-butyl 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)propanoate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2.1: dichloromethane / 0.83 h / 0 - 20 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C
5.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C
6.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere
7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
7.2: 1.75 h / -78 - 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)propanoic acid

2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2.1: dichloromethane / 0.83 h / 0 - 20 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C
5.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C
6.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere
7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
7.2: 1.75 h / -78 - 20 °C
8.1: hydrogenchloride / dichloromethane / 5 h / 0 - 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

6-bromo-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-3-ol

6-bromo-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-3-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

6-bromo-3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline

6-bromo-3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation
4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline-6-carbonitrile

3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation
4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C
5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.67 h / 140 °C / Inert atmosphere; Microwave irradiation
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

1-(3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-6-yl)cyclopropanamine

1-(3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-6-yl)cyclopropanamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation
4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C
5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.67 h / 140 °C / Inert atmosphere; Microwave irradiation
6: titanium(IV) isopropylate / tetrahydrofuran / 5.67 h / 20 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

4-chloro-N-(1-(3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-6-yl)cyclopropyl)benzamide 2,2,2-trifluoroacetate salt

4-chloro-N-(1-(3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-6-yl)cyclopropyl)benzamide 2,2,2-trifluoroacetate salt

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2: dichloromethane / 0.83 h / 0 - 20 °C
3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation
4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C
5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.67 h / 140 °C / Inert atmosphere; Microwave irradiation
6: titanium(IV) isopropylate / tetrahydrofuran / 5.67 h / 20 °C
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
View Scheme
1,2,3,4-tetrahydroquinolin-3-ol
3418-45-9

1,2,3,4-tetrahydroquinolin-3-ol

2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)-N-(4-chlorophenyl)propanamide

2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)-N-(4-chlorophenyl)propanamide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
2.1: dichloromethane / 0.83 h / 0 - 20 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C
5.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C
6.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere
7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
7.2: 1.75 h / -78 - 20 °C
8.1: hydrogenchloride / dichloromethane / 5 h / 0 - 20 °C
9.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C
View Scheme

3418-45-9Downstream Products

3418-45-9Relevant articles and documents

Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines

Kim, Eunae,Jeon, Hyun Ji,Park, Sehoon,Chang, Sukbok

supporting information, p. 308 - 313 (2019/11/13)

Described herein is an organoborane-catalysed consecutive borylative reduction of quinolines and isoquinolines to furnish tetrahydro(iso)quinolines bearing a C(sp3)?B bond β to the nitrogen atom. The installed C?B bond is oxidatively transformed to the hydroxy group in one pot. The present double hydroboration is proposed to proceed via a stepwise ionic mechanism involving a boronium ion. The stereo-outcome was found to be dependent on the position (C2 vs C4) of the substituents in quinolines. (Figure presented.).

4,5,6,7-TETRAHYDRO-1 H-PYRAZOLO[4,3-C]PYRIDIN-3-AMINE COMPOUNDS AS CBP AND/OR EP300 INHIBITORS

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Page/Page column 266, (2016/06/14)

The present invention relates to compounds of formula (I) or formula (II): and to salts thereof, wherein R1-R4 of formula (I) and R1-R3 of formula (II) have any of the values defined herein, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) of formula (II) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.

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