Hydrochloric Acid → 1-Methyl-3-phenyl-1H-indazole-6-carboxylic acid

HRID 1097001Notes

Reaction equation

[OH-].[Na+].C1COCC1.[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20]C)=[O:19])[CH:16]=2)[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:10]1.Cl>CO>[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=2)[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

In a 50-mL egg plant-type flask, aqueous 5 N sodium hydroxide solution (1.3 mL, 6.5 mmol) was added to a THF (5 mL)-methanol (5 mL) mixed solution of methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate (604 mg, 22 mmol), and stirred overnight at 60° C. With cooling with ice, aqueous 5 N hydrochloric acid solution (1.3 mL, 6.5 mmol) was added to the reaction solution, and concentrated to obtain a mixture of the title compound with salt, as a colorless solid.

Workup

additionwas added to the reaction solution
concentrationconcentrated
customto obtain

Sources & evidence

ORD record: ord-407f799f0ced4dadb7e66e7ce78a53e5
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138197B2

Reaction notes

Loading…