Triethylamine → 4-CYANAMINOBENZOIC ACID

Participants

Reaction Conditions

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, at 0° C. (ice bath), 12.65 g of methanesulfonyl chloride. The mixture was stirred for one hour at 0° C. then concentrated under reduced pressure. To the concentrate was added methanol. The resulting crystalline precipitate was collected by filtration and dissolved in 100 ml of methanol. To the solution was added, while stirring at room temperature, a solution of 12 g of sodium hydroxide in 100 g of water. The methanol was distilled off under reduced pressure. To the residue was added 700 ml of water. To this 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