Hydrochloric Acid → 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

HRID 1805189Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:7]=1)=[O:5])C.[OH-].[K+].Cl>CO>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:10]=2[CH3:11])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of the ester 3a (1.0 g, 2.44 mmol) in methanol (25 mL) was added potassium hydroxide (1.0 g, 17.86 mmol) in one portion. The resulting mixture was heated at 60° C. for 4 h. The reaction mixture was then poured into ice water, and the pH of the mixture was adjusted to acidic with addition of 10% hydrochloric acid. The precipitate formed was collected by filtration, washed with water, and dried under vacuum to give carboxylic acid 4a (0.88 g, 94%) as a white solid.

Workup

customThe precipitate formed
filtrationwas collected by filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-cbc20135648949aa9dd51e83482145d5
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354442B2

Reaction notes

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