3-Amino-1,2-benzisoxazole-6-carbonitrile → 3-Amino-1,2-benzisoxazole-6-methanamine
Reaction equation
CSC.B.[NH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]#[N:16])=[CH:14][C:9]=2[O:8][N:7]=1>COCCOC>[NH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][NH2:16])=[CH:14][C:9]=2[O:8][N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Borane methylsulfide complex (2 M in THF, 1.98 mL) was added to a stirred refluxing solution of 3-amino-6-cyano-1,2-benzisoxazole (210 mg, 1.32 mmol) in DME (10 mL). After 45 min excess methyl sulfide was evaporated and the reaction mixture was cooled and quenched with 1M HCl solution (10 mL). The mixture was stirred for 30 min and then was neutralised with sodium bicarbonate solution and concentrated to dryness. The residue was triturated with 5% methanol/chloroform, filtered and the filtrate evaporated in vacuo. The residue was purified by chromatography on silica (5% methanol, chloroform/ammonia) to give the title compound as a yellow solid: