Methanol → 3,5-Diamino-2-methylbenzoic acid

Participants

Reaction Steps

3,4-Diaminobenzoic acid (3.0 g) was suspended in methanol, followed by the dropwise addition of 1.86 ml of thionyl chloride. Thionyl chloride was added twice, in an amount of 0.5 ml each time, and the resulting mixture was heated under reflux for 10 hours and 40 minutes. The thionyl chloride and methanol were distilled out, followed by the dissolution of the residue in methylene chloride. The solution so formed was washed with a 0.5N aqueous solution of sodium hydroxide and then with a saturated aqueous solution of sodium chloride, and was dried over sodium sulfate. The solvent was distilled out. The residue was washed with n-hexane and then dried, whereby 3.04 g of the target compound were obtained (yield: 93%).

Provenance & Evidence