Acetyl chloride → 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 through celite and the filtrate concentrated under reduced pressure. A mixture of the residue, triethylamine (1.8 mL, 12.9 mmol) and acetyl chloride (1.38 mL, 19.35 mmol) in dichloromethane (15 mL) was stirred at ambient temperature for 1 hour, poured into 1N NaOH (20 mL) and methanol (20 mL). After 10 minutes, the mixture was concentrated under reduced pressure and taken up in ethyl acetate and 1N HCl (50 mL, 1:1). The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated to provide titled compound. MS (ESI (−)) m/e 166(M−H)+; 1H NMR (300 MHz, DMSO-d6) 9.31(s, 2H), 6.86 (t, 1H), 6.34 (d, 2H), 2.11(s, 3H).

1. filtrationThe reaction mixture was filtered through celite
2. concentrationthe filtrate concentrated under reduced pressure
3. stirringwas stirred at ambient temperature for 1 hour
4. waitAfter 10 minutes
5. concentrationthe mixture was concentrated under reduced pressure
6. customThe layers were separated
7. washthe organic phase was washed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-19421e436a09411090786819f649aded

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06972340B2