p-Toluenesulfonic acid → 8-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol

HRID 2266433Notes

Reaction equation

HRID 2266433 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][CH:16]([C:20](=O)[CH3:21])[C:17](=O)[CH3:18])=[CH:13][CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:8][C:7]1[C:2]2[N:1]=[C:20]([CH3:21])[C:16]([CH2:15][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:24][CH:23]=3)=[C:17]([CH3:18])[C:3]=2[C:4]([OH:9])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14888033-[(4-Chlorophenyl)methyl]pentane-2,4-dioneHCID 50700783-Amino-4-chlorophenol

Product 1

HCID 1363358958-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol

Conditions

Temperature
170 °C

Procedure

A mixture of 3-amino-4-chlorophenol (2.2 g), 3-(4-chlorobenzyl)pentane-2,4-dione (3.4 g) and toluene-4-sulfonic acid (few crystals) was heated at 170° C. under nitrogen for 10 hours. The mixture was cooled to room temperature and purification by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (1:19 by volume), followed by trituration with diethyl ether gave title compound as a pale brown solid, 0.41 g.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompurification by column chromatography on silica gel
  3. washeluting with a mixture of methanol and dichloromethane (1:19 by volume)

Sources & evidence

ORD record
ord-9072f5048bb44391bd4d0021e3b262d8
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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