Dichloromethane → (R,S)-N-(alpha-(1-Hydroxyethyl)benzyl]-3-methyl-2-phenylquinoline-4-carboxamide

HRID 2394814Notes

Reaction equation

HRID 2394814 reaction equation
[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12](Cl)=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:21]1([CH:27]([NH2:31])[CH:28]([OH:30])[CH3:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)Cl>CC#N>[OH:30][C@H:28]([C@H:27]([NH:31][C:12]([C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:2]=1[CH3:1])=[O:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 123529221-Amino-1-phenylpropan-2-olHCID 227143263-Methyl-2-phenylquinoline-4-carbonyl chloride

Product 1

HCID 131720840(R,S)-N-(alpha-(1-Hydroxyethyl)benzyl]-3-methyl-2-phenylquinoline-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared as described in Ex. 1, starting from 11.08 g (39.33 mmol) of crude 3-methyl-2-phenylquinoline-4-carbonylchloride, 4.87 g (32.20 mmol) of 1-phenyl-2-hydroxypropylamine and 10.33 ml (74.14 mmol) of TEA in 150 ml of a 1:1 mixture of dry CH2Cl2 and CH3CN.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-411bcb34c6dc43a8acd6616019cc9ff9
Source dataset
uspto-grants-1998_09
Patent number
US05811553

Reaction notes

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