4-Methylmorpholine → HCID 3091375, compound

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).

1. washwashed with saturated NaHCO3 (2×50 mL), 1N HCl (2×50 mL) and brine (2×50 mL)
2. dry with materialdried over Na2SO4
3. customAfter evaporation of the solvent
4. dissolutionthe residue was dissolved in THF (50 mL)
5. addition2N NaOH (10 mL) was added
6. temperaturethe mixture heated to 60° C. for 2 hours
7. extractionAfter neutralization with 1N HCl, the mixture was extracted with ethyl acetate (4×50 mL)
8. washthe organic phase was washed with brine (2×50 mL)
9. dry with materialdried over Na2SO4
10. customevaporated

ORD record

ord-5d9b25b95d894dd1be818ddc25314f49

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05741819