m-Toluohydrazide → 3-Methyl-benzoic acid [1-(3-chloro-2-hydroxy-phenyl)-methylidene]-hydrazide

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-chloro-2-hydroxy-benzaldehyde (0.100 g, 0.639 mmol) and 3-methyl-benzoic acid hydrazide (0.096 g, 0.639 mmol) in ethanol (2 mL) was heated to 60° C. for 18 hours. The reaction mixture was cooled to room temperature to precipitate the product. The solid was collected via suction filtration and rinsed with ethanol to furnish 3-methyl-benzoic acid [1-(3-chloro-2-hydroxy-phenyl)-methylidene]-hydrazide as a white solid (0.046 g, 25%): mp 166-169° C.; 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=12.0 Hz, 1H), 7.76 (d, J=10.0 Hz, 2H), 7.47 (dd, J=15.6, 6.2 Hz, 4H), 6.97 (t, J=7.8 Hz, 1H), 2.39 (d, J=12.0 Hz, 3H); ESIMS m/z 289 ([M+H]+), 287 ([M−H]−).

Provenance & Evidence