Hydrazine hydrate (1:1) → 3-bromo-4-methylbenzohydrazide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl-3-bromo-4-methylbenzoate (5.0 g, 21.8 mmol, 1.0 eq) and hydrazine hydrate (5 mL, 99 mmol, 4.5 eq) in methanol (50 mL) was heated to 80° C. overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated under vacuum. The residue was taken in ethyl acetate (100 mL) and washed with water (2×50 mL), brine (50 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under reduced pressure to afford 2.5 g (50%) of the desired product as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H, D2O exchangeable), 8.02 (d, J=1.0 Hz, 1H), 7.74 (dd, J=1.0, 8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 3.35 (s, 2H, D2O exchangeable), 2.38 (s, 3H); ESI-MS (m/z) 229, 231 [(MH)+, Br79,81].

Provenance & Evidence