Methanol → N-(2,6-dihydroxyphenyl)acetamide

A mixture of 2-nitroresorcinol (1.0 g, 6.45 mmol) and 10% Pd—C (100 mg) in methanol (15 mL) was stirred under an atmosphere of hydrogen at ambient temperature for 4 hours. The reaction mixture was filtered and concentrated to get desired aniline. The aniline was then dissolved in dichloromethane (15 mL). Triethylamine (1.8 mL, 12.9 mmol) was added, followed by acetyl chloride (1.38 mL, 19.35 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, and added 20 mL 1N NaOH and methanol (20 mL). After 10 minutes, the mixture was concentrated and taken in ethyl acetate and 1N HCl. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to provide titled compound. MS (ESI (+)) m/e 168(M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.31(s, 2H), 6.86 (t, J=8.1 Hz, 1H), 6.34 (d, J=8.1 Hz, 2H), 2.11(s, 3H).

1. waitAfter 10 minutes
2. concentrationthe mixture was concentrated
3. washThe organic phase was washed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-daed40609cad4502b35aae2fa906808d

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169797B2