p-Toluenesulfonic acid → 3-(4-Chlorobenzyl)-2,4,7-trimethylquinolin-5-ol

HRID 2266430Notes

Reaction equation

HRID 2266430 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[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:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][C:16]2[C:20]([CH3:21])=[N:1][C:2]3[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([OH:9])[C:3]=3[C:17]=2[CH3:18])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14888033-[(4-Chlorophenyl)methyl]pentane-2,4-dioneHCID 30186673-Amino-5-methylphenol

Product 1

HCID 1363463303-(4-Chlorobenzyl)-2,4,7-trimethylquinolin-5-ol

Conditions

Temperature
160 °C

Procedure

A mixture of 3-amino-5-methylphenol (1.0 g), 3-(4-chlorobenzyl)pentane-2,4-dione (1.7 g) and toluene-4-sulfonic acid (0.30 g) was heated at 160° C. under nitrogen for 3 hours. The mixture was cooled to room temperature and the residue triturated with methanol to give title compound, 1.5 g.

Workup

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

Sources & evidence

ORD record
ord-f1acf58de28a45b6a0f12da71a887aaa
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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