Hydrazine hydrate (1:1) → 3-Cyanobenzohydrazide

HRID 732027

Reaction equation

HRID 732027 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

HCID 24654Hydrazine hydrate (1:1)HCID 83554Benzoic acid, 3-cyano-, methyl ester

Product 1

HCID 219426583-CyanobenzohydrazideYield 52.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9de038fd9408409d98c15b6450e01aa9
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

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