Triethylamine → 4-CYANAMINOBENZOIC ACID

Participants

Reaction Steps

In 180 ml of tetrahydrofuran was dissolved 17.12 g of 4-amino(N-hydroxyimino)methylbenzoic acid methyl ester. To the solution was added 12.12 g of triethylamine. To the mixture was added dropwise, on an ice-bath, 12.65 g of methanesulfonyl chloride. The mixture was stirred for one hour under the same conditions, followed by concentration under reduced pressure. To the concentrate was added methanol. The resulting crystalline precipitate was collected by filtration, which was dissolved in 100 ml of methanol. To the solution was added, while stirring at room temperature, 100 g of water containing 12 g of sodium hydroxide. Methanol was distilled off under reduced pressure. To the residue was added 700 ml of water. To the mixture was added, while stirring at room temperature, 80 ml of 4N HCl. The resulting crystalline precipitate was collected by filtration to give 13.12 g of the title compound as a colorless crystalline product.

Provenance & Evidence