3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)

Base Information

• Chemical Name: 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)
• CAS No.: 145554-63-8
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.208
• Mol file: 145554-63-8.mol

Synonyms:3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)

Chemical Property of 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

(R)-1,2,3,4-tetrahydro-3-Quinolinamine 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI)

There total 11 articles about 3-Quinolinamine,1,2,3,4-tetrahydro-,(R)-(9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

3-aminoquinoline (580-17-6) → 3(R,S)-amino-1,2,3,4-tetrahydroquinoline (40615-02-9,145554-63-8)

Guidance literature:

3-aminoquinoline; With H₂SiEt₂; tris(pentafluorophenyl)borate; In chloroform; at 100 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1055/s-0036-1588442

Reference yield:

Cbz-D-Phe (2448-45-5) → (3R)-1,2,3,4-tetrahydroquinolin-3-amine (145554-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; dichloromethane / 24 h / 20 °C

2: bis-[(trifluoroacetoxy)iodo]benzene; trifluoroacetic acid / dichloromethane / 1.17 h / 0 °C

3: hydrogen; palladium 10% on activated carbon / ethanol / 2585.81 Torr

4: dimethyl sulfide borane / tetrahydrofuran / 120 h / 0 - 20 °C / Reflux

With palladium 10% on activated carbon; hydrogen; dimethyl sulfide borane; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/acs.jmedchem.5b01612

Reference yield:

(3S)-3-amino-3,4-dihydro-1H-quinolin-2-one (40615-17-6) → (3S)-1,2,3,4-tetrahydroquinolin-3-amine (145554-63-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 40 ℃; for 2h;

upstream raw materials:

3-aminoquinoline

D-(R)-phenylalanine

Cbz-D-Phe

(R)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one

Downstream raw materials:

(5R)-5-amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-1(2H)-one

U 91356

rac-8-[(2,6-difluorobenzyl)oxy]-2-methyl-N-(1,2,3,4-tetrahydroquinolin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

Refernces

• 1、 Gao, Chao,Xuan, Qingqing,Song, Qiuling. "Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution". supporting information. p. 2504 - 2508. Retrieved 2021/07/31.
• 2、 Gandhamsetty, Narasimhulu,Park, Sehoon,Chang, Sukbok. "Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes". supporting information. p. 2396 - 2400. Retrieved 2017/11/04.