Ethyl 2-(4-chlorobenzyl)acetoacetate → 3-(4-chlorobenzyl)-5-hydroxy-4,7-dimethyl-1H-quinolin-2-one

HRID 2266424Notes

Reaction equation

HRID 2266424 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O:12][C:13](=O)[CH:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:15](=O)[CH3:16])C>>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:14]2[C:13](=[O:12])[NH:1][C:2]3[C:3]([C:15]=2[CH3:16])=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=3)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2757404Ethyl 2-(4-chlorobenzyl)acetoacetateHCID 30186673-Amino-5-methylphenol

Product 1

HCID 686078103-(4-chlorobenzyl)-5-hydroxy-4,7-dimethyl-1H-quinolin-2-one

Conditions

Temperature
150 °C

Procedure

A mixture of 3-amino-5-methylphenol (0.25 g) and 2-(4-chlorobenzyl)-3-oxobutyric acid ethyl ester (0.52 g) was heated at 150° C. under nitrogen for 7 hours. The mixture was cooled to room temperature and the residue triturated with methanol to afford the title compound as an off-white solid, 0.32 g.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe residue triturated with methanol

Sources & evidence

ORD record
ord-7a72b69559d34cdf9f0ff20fac4dbd97
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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