Aniline → HCID 131716908, compound

Participants

Reaction Steps

A mixture of the aniline (Intermediate 82, 20 g, 94 mmol), sodium bicarbonate (11.8 g, 141 mmol) and methyl chloroacetate (9.1 ml, 103 mmol) in acetonitrile (30 ml) was heated at 90°-100° for 24 h. Water (200 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with 2N hydrochloric acid (2×100 ml), water (2×100 ml) and brine (100 ml) before drying (Na2SO4) and evaporating to an orange solid. Trituration with ether, followed by evaporation of the triturate gave the title compound (Intermediate 83) as a pale grey solid (16 g; 60%), m.p. 78°-80°.

Provenance & Evidence