Ammonia → HCID 86721347, compound

[step 1] 2-Methoxy-6-nitroaniline (4.0 g, 23.8 mmol) was dissolved in DMA (24 mL), pyridine (5.8 mL, 71.4 mmol) and 2-methoxyacetyl chloride (6.5 mL, 71.4 mmol) were added at 0° C., and the mixture was stirred at room temperature for 1 hr. Under ice-cooling, methanol and aqueous ammonia solution were added to the mixture, and the mixture was stirred at room temperature for 30 min. Water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-30/70 v/v) to give 2-methoxy-N-(2-methoxy-6-nitrophenyl)acetamide (5.4 g, 95%).

1. temperatureUnder ice-cooling
2. stirringthe mixture was stirred at room temperature for 30 min
3. extractionthe mixture was extracted 3 times with ethyl acetate
4. washThe combined organic layers were washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-30/70 v/v)

ORD record

ord-eedbf64f130043c5ad5569b00afa7111

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969345B2