Cl.[CH2:2]([NH:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:11](=O)[C:12]([CH3:14])=[O:13]>O.C(Cl)Cl>[CH2:2]([NH:9][N:10]=[CH:11][C:12](=[O:13])[CH3:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1To a solution of benzylhydrazine hydrochloride (11.1 g, 57.1 mmol) in water (100 mL) was added dropwise a solution of pyruvaldehyde (10.3 g, 9.3 mL, 57.1 mmol) in water (500 mL). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (4×150 mL). The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to provide 2-oxopropanal benzylhydrazone (10.1 g, 100%).
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