Methanol → 3-Cyanobenzohydrazide

Participants

Reaction Conditions

Reaction Steps

3-cyanobenzoyl chloride (4.8 g, 29.0 mmol) was dissolved in DCM (20 ml) and MeOH (40 ml) was added in portions at 0° C. The mixture was stirred at 0° C. for 1 h and at rt for 2 h. The solvents were evaporated and the crude methyl ester was dissolved in EtOH (50 ml) and hydrazine (24% aq., 9 ml, 45 mmol) was added. The reaction mixture was refluxed for 48 h and the solvents were evaporated (coevaporation with water). The residue was purified with prep. HPLC to give the title compound (1.8 g, 39%). 1H NMR (DMSO-d6): 9.98 (br s, 1 H), 8.21 (m, 1 H), 8.13 (m, 1 H), 7.99 (m, 1 H), 7.69 (t, 1 H), 4.61 (br s, 2 H).

Provenance & Evidence