Methanol → 5-Acetyl-N-methyl-N-propyl-isophthalamic acid

Participants

Reaction Steps

To a solution of methyl 3-acetyl-5-(methyl(propyl)carbamoyl)benzoate (107 mg, 0.386 mmol) in a mixture of THF (0.4 mL), MeOH (0.8 mL) and H2O (2.0 mL), was added LiOH (28 mg, 1.159 mmol) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The aqueous layer was washed with ethyl acetate twice and acidified with 1N HCl solution to pH around 2˜3. The aqueous layer was extracted with ethyl acetate 3 times and the combined organic layers were dried over sodium sulfate and concentrated under vacuum to give the title compound which was ready for next step without further purification: HPLC retention time: 1.412 min (method A). MS (ESI) (M+H)+ 264.18.

Provenance & Evidence