Acetyl chloride → HCID 58964491, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-methylamino-4-trifluoromethyl-benzoic acid methyl ester (26 mg, 0.96 mmoles) is dissolved in dioxane and after addition of acetyl chloride (54 μL, 1 eq.) the mixture is stirred for 2 h (TLC control) at 80° C. Acetyl chloride (0.9 eq.) is then added and stirring continued for 18 hours at 80° C. The mixture is evaporated to dryness. The residue is dissolved in dichloromethane, filtrated, evaporated and dried under HV. The crude product is purified by flash-chromatography (gradient hexane to ethyl acetate, silicagel) to yield 5-(acetyl-methyl-amino)-2-amino-4-trifluoromethyl-benzoic acid methyl ester as a yellow solid (36 mg, 12.8% yield) (MH+291, Rt 5.0 min.). The other monoacetyl derivative (50 mg) and the diacetyl derivative (92 mg) are also isolated.

Provenance & Evidence