Hydrazine hydrate (1:1) → 3-Cyanobenzohydrazide
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=1.O.[NH2:14][NH2:15]>C(O)C>[C:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([NH:14][NH2:15])=[O:2])#[N:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-cyano-benzoic acid methyl ester (2 g, 12 mmol) and hydrazine monohydrate (0.60 mL, 12 mmol) in ethanol (10 mL) was stirred at room temperature overnight. The reaction mixture was concentrated and then the residue was triturated with diethyl ether to afford 3-cyano-benzoic acid hydrazide (1.02 g, 51%, pink solid). 1H NMR (DMSO) □ (ppm): 10.31 (s, 1H), 8.21 (m, 1H), 8.11 (m, 1H), 7.99 (m, 1H), 7.70 (m, 1H), 4.50 (s, 1H).
Workup
- concentrationThe reaction mixture was concentrated
- customthe residue was triturated with diethyl ether
Sources & evidence
- ORD record
- ord-9de038fd9408409d98c15b6450e01aa9
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585881B2
Reaction notes
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