p-Toluidine → HCID 14551372, compound

Participants

Reaction Steps

To a solution of p-toluidine (119.4 g) in conc. aqueous HCl (575 ml) was added a solution of NaNO2 (84.6 g) in water (500 ml) at 0°-5° C. during 1.5 h. The reaction mixture was added in one portion to a mixture of methyl 2-(4-fluorobenzyl)-3-oxobutanoate (250 g), KOH (220 g), water (0.5 l), ethanol (1.25 l) and ice (2 kg) under stirring. After reaction for 2 h at room temperature the reaction mixture was extracted with diethyl ether (2×2 l). The combined organic phases were washed with water (3 l) and dried (Na2SO4). Evaporation of the solvents afforded the crude 4-tolylhydrazone of methyl 2-oxo-3-(4-fluorophenyl)-propanoate (330 g), which was used without further purification.

Provenance & Evidence