(R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline

Base Information

• Chemical Name: (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline
• CAS No.: 1416892-65-3
• Molecular Formula: C₁₇H₂₀N₂
• Molecular Weight: 252.359
• Mol file: 1416892-65-3.mol

Synonyms:

Chemical Property of (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline

There total 3 articles about (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline 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:

2-(4-(dimethylamino)phenyl)quinoline (16032-41-0) → (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline (1416892-65-3)

Guidance literature:

With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; methyl[(1,1′-biphenyl-2-yl)di-tert-butyl phosphine]gold(I); diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2-methoxy-phenylamine; In chloroform; at 35 ℃; for 16h; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c2cc37623g

Reference yield:

2-(4-(dimethylamino)phenyl)quinoline (16032-41-0) → (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline (1416892-65-3) + (S)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline

Guidance literature:

With C₅₇H₃₀B₂F₂₀*2C₅H₅N; hydrogen; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; at -20 ℃; for 24h; under 37503.8 Torr; Overall yield = 94 %; enantioselective reaction; Autoclave;

DOI:10.1002/anie.201900907

Reference yield:

o-aminobenzaldehyde (529-23-7) + 4-ethynyl-N,N-dimethylaniline (17573-94-3,752235-18-0) → (R)-N,N-dimethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)aniline (1416892-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: methyl[(1,1′-biphenyl-2-yl)di-tert-butyl phosphine]gold(I); (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 2-methoxy-phenylamine / chloroform / 16 h / 60 °C / Inert atmosphere; Molecular sieve

2: methyl[(1,1′-biphenyl-2-yl)di-tert-butyl phosphine]gold(I); (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 2-methoxy-phenylamine; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / chloroform / 16 h / 35 °C / Inert atmosphere

With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; methyl[(1,1′-biphenyl-2-yl)di-tert-butyl phosphine]gold(I); diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2-methoxy-phenylamine; In chloroform;

DOI:10.1039/c2cc37623g

upstream raw materials:

o-aminobenzaldehyde

4-ethynyl-N,N-dimethylaniline

2-(4-(dimethylamino)phenyl)quinoline