Methyl iodide → 2-(Methylamino)-4-nitrophenol

Temperature

40 °C

Triethylamine (2 ml, 14.4 mmol) was added to a solution of 2-amino-4-nitrophenol (1) (1.54 g, 10 mmol) and methyl iodide (1 ml, 16 mmol) in methanol (10 ml). After 1 hour at 40° C., further methyl iodide (1 ml) and triethylamine (1 ml) were added and the mixture was stirred at 40° C. for a further 2 hours. The reaction mixture was concentrated to dryness in vacuo, the residue was added to aqueous 2N sodium acetate solution and the mixture was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and chromatographed on silica gel (eluent dichloromethane/methanol 95/5). Yield 880 mg (52%).

1. concentrationThe reaction mixture was concentrated to dryness in vacuo
2. additionthe residue was added to aqueous 2N sodium acetate solution
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialThe organic phase was dried with sodium sulfate
5. customchromatographed on silica gel (eluent dichloromethane/methanol 95/5)

ORD record

ord-66aae1aa20a84164b9801f127695ea82

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05935995