Dichloromethane → HCID 735094, compound

Participants

Reaction Steps

To 5.0 g (33 mmol) of the methyl 3-aminobenzoate (11) prepared in Example 1 in 70 mL of methylene chloride containing 4.0 mL (36 mmol) of N-methylmorpholine was added 7.49 g (33 mmol) of 2-naphthalenesulfonyl chloride. After stirring at room temperature overnight, the reaction mixture was quenched with 1N HCl (100 mL). The suspension was dissolved in ca. 250 mL of THF and enough ether was added to induce phase separation. The organic extract was washed with saturated sodium chloride solution (2×). The organic phase was dried (MgSO4), and concentrated to give 11.0 g (97% yield) of the title compound as a pale yellow solid: 1H-NMR (200 MHz; DMSO-d6) δ 8.46 (s, 1H), 8.13 (t, 2H), 7.99 (d, 1H), 7.55-7.75 (m, 5H), 7.43 (dd, 21H), 7.38 (d, 1H), 3.79 ppm (s, 3H).

Provenance & Evidence