Hydroxyamine hydrochloride → 3-Cyano-2-hydroxy-5-methylbenzoic acid

Participants

Reaction Steps

3-Formyl-5-methylsalicylic acid (3.6 g) was dissolved in dimethylformamide (20 ml) and treated with hydroxylamine hydrochloride (1.53 g). The mixture was heated at reflux for 10 minutes and then the solvent was removed in vacuo. The residue was treated with water (20 ml) and hydrochloric acid (2N; 10 ml). The precipitated solid was filtered off and recrystallized from aqueous ethanol to give 3-cyano-5-methylsalicylic acid (2.7 g), m.p. 193°-194° C.

Provenance & Evidence