Hydrogen Peroxide → Methyl 4-aminocarbonyl-5-(isopropylamino)-2-methylbenzoate

Participants

Reaction Steps

Methyl 4-cyano-5-(isopropylamino)-2-methylbenzoate (224 mg, 0.96 mmol) was dissolved in DMSO (2 mL) and cooled in a cold water bath. 30% Aqueous hydrogen peroxide (0.2 mL) and potassium carbonate (42.6 mg, 0.31 mmol) was added, and the mixture was stirred at ambient temperature for 1 h. The reaction mixture was partitioned between ethyl acetate and 10% aqueous lithium chloride. The aqueous portion was extracted with ethyl acetate. The combined organic portion was dried over sodium sulfate, then filtered and concentrated to a yellow oil which was purified by column chromatography (silica gel, 15-30% ethyl acetate in hexanes to afford methyl 4-aminocarbonyl-5-(isopropylamino)-2-methylbenzoate (202 mg, 0.81 mmol, 83% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.35 (d, 1H), 7.26 (d, 1H), 7.24-7.22 (m, 2H), 5.70 (br s, 1H), 3.90 (s, 3H), 3.75-3.68 (m, 1H), 2.42 (s, 3H), 1.26-1.24 (m, 6H); MS (EI) for C13H18N2O3: 251 (MH+).

Provenance & Evidence