4-Methylmorpholine → HCID 3091375, compound

Participants

Reaction Steps

To 1.51 g (10 mmol) of the methyl 3-aminobenzoate prepared in Example 1 in 40 mL of methylene chloride containing 2 mL of N-methylmorpholine was added 2.21 g (10 mmol) of 3-nitrobenzenesulfonyl chloride. After stirred at room temperature for 3 hours, methylene chloride (200 mL) was added and washed with saturated NaHCO3 (2×50 mL), 1N HCl (2×50 mL) and brine (2×50 mL) and dried over Na2SO4. After evaporation of the solvent, the residue was dissolved in THF (50 mL), 2N NaOH (10 mL) was added and the mixture heated to 60° C. for 2 hours. After neutralization with 1N HCl, the mixture was extracted with ethyl acetate (4×50 mL) and the organic phase was washed with brine (2×50 mL), dried over Na2SO4 and evaporated to give 3.05 g (94%) of the title compound as a white solid: 1H-NMR (300 MHz, DMSO-d6): δ 7.38 (m, 2H), 7.65 (t, 1H), 7.70 (s, 1H), 7.87 (t, 1H), 8.13 (dd, 1H), 8.47 (dd, 1H), 8.50 (t, 1H), 10.81 (s, 1H), 13.11 (s, 1H).

Provenance & Evidence