Ethanol → 7-chloro-1H-indazole-5-carboxylic acid

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=C(C#N)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[OH-:13].[K+].[CH2:15]([OH:17])[CH3:16]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:16]([C:15]([OH:13])=[O:17])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Komponenten

Versuchsvorschrift

To a solution of 7-chloro-1H-indazole-5-carbonitrile (250 mg, 1.41 mmol) in ethanol/water (3:1 ration, 15 mL) was added potassium hydroxide (395 mg, 7.04 mmol) and the mixture was heated at reflux. After 3 houra, the majority of the ethanol was allowed to distill off, additional potassium hydroxide (614 mg) was added and heating was continued for overnight. The reaction mixture was cooled to room temperature, washed with Et2O (3×20 mL) and the organic extract was acidified with 1 N HCl. The resultant precipitate was isolated by vacuum filtration, washed with water (about 15 mL) and heptane (about 15 mL), dried at room temperature/0.5 mmHg to provide the title compound (221 mg, 79.7%).