Acetic Acid → HCID 13885833, compound

Participants

Reaction Steps

A mixture of 8.4 g (0.075 mole) of potassium tert.-butoxide in 200 ml of tetrahydrofuran (under a nitrogen atmosphere) was stirred and cooled in an ice bath. A solution of 13.7 g (0.046 mole) of 2-[(cyanomethyl)phenylamino]-5-methoxybenzoic acid methyl ester in 150 ml of tetrahydrofuran was added over two hours, the ice bath was removed, and the new mixture was stirred for an additional 42 hours. The total reaction mixture was added to 1.1 kg of ice/water and acidified with 12.0 ml of glacial acetic acid to precipitate the crude product. The solid was filtered, washed with water, and recrystallized from aqueous methanol to yield 10.3 g (84% yield) of the nitrile product. A sample recrystallized again as above was analytically pure, mp 182° C.-dec.

Provenance & Evidence