Hydroxyamine hydrochloride → 3-Phenyl-1H-5-indazolecarbonitrile
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.Cl.[NH2:19]O.C([O-])=O.[Na+]>C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 22 g of 5-formyl-3-phenylindazole, 8 g of hydroxylamine hydrochloride and 12.5 g of sodium formate was added to 150 ml of formic acid, and after refluxing for 2 hours, the mixture was extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to give 16.5 g of 5-cyano-3-phenylindazole (m.p. 150°-151° C.).