Ammonia → N-(5-Amino-1H-indazol-3-yl)benzamide

HRID 25384Notes

Reaction equation

HRID 25384 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-])=O.C(O)C.N>O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 22319544N-(5-nitro-1H-indazol-3-yl)benzamide

Product 1

HCID 22319522N-(5-Amino-1H-indazol-3-yl)benzamideYield 74.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(5-Amino-1H-indazol-3-yl)benzamide can be obtained as described in Example 4 from 0.6 g of N-(5-nitro-1H-indazol-3-yl)benzamide, 21 ml of ethanol, 4.2 g of ferrous sulfate, 6.6 ml of water and 5.1 ml of 32% aqueous ammonia. 0.4 g of N-(5-amino-1H-indazol-3-yl)benzamide is thus obtained in the form of a yellow powder melting at 116° C.

Sources & evidence

ORD record
ord-8876c742c4ff4aecb28b8f589c22d8b3
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

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