Hydrochloric Acid → 3-(2-Chlorophenyl)-1-(4-methylphenyl)-1H-indazole-6-carboxylic acid

HRID 1047625Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=2)[N:10]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[N:9]=1.[OH-].[Na+].Cl>CO.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)[N:10]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 3-(2-chlorophenyl)-1-(4-methylphenyl)-1H-indazole-6-carboxylate (0.25 g, 0.66 mmol) in methanol (1.5 mL) and tetrahydrofuran (2.9 mL) was added sodium hydroxide (1.0 M, 3.98 mL, 3.98 mmol). The mixture was heated to 50° C. and stirred for 1.5 h. The mixture was cooled to ambient temperature and 1.0 M hydrochloric acid (ca 4.0 mL) was added until pH<3. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with saturated aqueous sodium chloride (1×7 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.24 g): LC-MS [M+1]=363.2.

Workup

temperatureThe mixture was cooled to ambient temperature
extractionThe mixture was extracted with ethyl acetate (3×10 mL)
washThe combined organic layers were washed with saturated aqueous sodium chloride (1×7 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6d8d23811acb426a8a922bd7ffe7acdf
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569512B2

Reaction notes

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