Aniline → HCID 178496274, compound

Participants

Reaction Steps

To a solution of aniline (50 g) in 6N hydrochloric acid (536 mL) was added dropwise with stirring under ice-cooling an aqueous solution (142 mL) of sodium nitrite (55.6 g). The solution was added dropwise to a mixed solution of methyl 4-methoxy-3-oxobutanoate (78.5 g) and sodium acetate (264 g) in methanol/water (1.4 L/0.35 L) with stirring under ice-cooling. The total amount was added dropwise, and the mixture was stirred at the same temperature for 2 hr. Water was added to the reaction mixture, and the mixture was stirred for 30 min. The precipitated yellow crystals were collected by filtration, washed successively with water, ethanol/diisopropyl ether (1/9) and diisopropyl ether, and dry to give the title compound (111.2 g) as yellow crystals.

Provenance & Evidence