Hydrochloric Acid → 1-Cyclobutyl-1H-indazole-3-carboxylic acid

HRID 602459Notes

Reaction equation

[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([C:14]([O:16]C)=[O:15])=[N:6]2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([C:14]([OH:16])=[O:15])=[N:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

The mixture of methyl 1-cyclobutyl-1H-indazole-3-carboxylate (2.21 g, 9.60 mmol, step 1 of Example 4), 2 N aqueous sodium hydroxide solution (9.6 mL, 1.92 mmol), and ethanol (30 mL) was stirred at 60° C. for 2 h. After cooling to room temperature, 2 N hydrochloric acid (9.6 mL) was added, and the solvent was removed under reduced pressure. The residue was suspended in tetrahydrofuran (100 mL), and the solution was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to give 1.90 g (92%) of the title compound as a white solid. This material was used for the next step without further purification.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed under reduced pressure
filtrationthe solution was filtered through a pad of Celite
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-06acb857c9a54d7bb21b819c802755e8
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906532B2

Reaction notes

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