Hydrochloric Acid → 1-methyl-6-(trifluoromethyl)-1H-indazole-3-carboxylic acid

HRID 511837Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[C:4]([C:15]([O:17]C)=[O:16])=[N:3]1.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:13])([F:14])[F:12])[CH:9]=2)[C:4]([C:15]([OH:17])=[O:16])=[N:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a tetrahydrofuran (2 mL) of methyl 1-methyl-6-(trifluoromethyl)-1H-indazole-3-carboxylate (50 mg, 0.19 mmol) was added 2N sodium hydroxide (0.2 ml, 4.0 mmol) at room temperature. The mixture was refluxed at 90° C. with stirring for 3 hours. After being cooled to room temperature, 2N hydrochloric acid was added to the mixture until pH became 4.0. The organic layer was extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. After the filtration to separate solvent and magnesium sulfate, the solvent was removed under reduced pressure to give 47 mg (quantitative yield) of the title as a white solid that was used in the next step without further purification;

Workup

temperatureAfter being cooled to room temperature
extractionThe organic layer was extracted with ethyl acetate
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationAfter the filtration
customto separate solvent and magnesium sulfate
customthe solvent was removed under reduced pressure
customto give 47 mg (quantitative yield) of the title as a white solid that
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-6579fd8e7f644ad7aa00b6a1c1a42870
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09101616B2

Reaction notes

Loading…