2-Chloro-4-phenylquinoline → Methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)amino]hexanoate

HRID 2396517Notes

Reaction equation

HRID 2396517 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25]>>[CH3:28][C:23]([CH3:29])([CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[C:24]([O:26][CH3:27])=[O:25]

Participants

3

Reactant 2

HCID 23066872-Chloro-4-phenylquinolineHCID 15681405Methyl 6-amino-2,2-dimethylhexanoate

Product 1

HCID 10474677Methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)amino]hexanoate

Procedure

A mixture of 3.2 g of 2-chloro-4-phenyl-quinoline (prepared according to the method of S. Kwon and K. Isagawa, Yoki Gosei Kagaku Shi 1973,31, 313) and 5.9 g of methyl 6-amino-2,2-dimethylhexanoate is heated to 100 C. for 8 hours. After cooling, the residue is purified by chromatography on silica gel (eluent: 98:2 dichloromethane/methanol). to give methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)amino]hexanoate obtained as an oil.

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. customthe residue is purified by chromatography on silica gel (eluent: 98:2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-539ee989d1944f5f8e3f71b8dcbe5930
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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