p-Toluenesulfonic acid monohydrate → 7-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol

HRID 2266447

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl: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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClC1C=C(O)C=C2C=1C(C)=C(CC1C=CC(Cl)=CC=1)C(C)=N2>CO>[Cl:8][C:6]1[CH:5]=[C:4]([OH:9])[C:3]2[C:17]([CH3:18])=[C:16]([CH2:15][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:24][CH:23]=3)[C:20]([CH3:21])=[N:1][C:2]=2[CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-amino-5-chlorophenol (0.46 g), 3-(4-chlorobenzyl)pentane-2,4-dione (0.72 g), and p-toluenesulfonic acid monohydrate (0.26 g) was heated at 160° C. for 2 hours. The mixture was cooled to room temperature, diluted with methanol (5.0 mL) and sonicated. The resulting precipitate was collected by filtration, washed with methanol and dried to afford a 50:50 mixture of title compound and 5-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-7-ol as an off-white solid, 0.67 g.

Workup

temperatureThe mixture was cooled to room temperature
customsonicated
filtrationThe resulting precipitate was collected by filtration
washwashed with methanol
customdried
customto afford

Sources & evidence

ORD record: ord-2eda990c044447b0b2d27e0e8d3449e5
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Linked notes

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