Acetyl chloride → N-Acetyl-N-(3-methoxyphenyl)hydroxylamine

Under ice-cooling, 10% palladium on activated carbon (0.46 g) and hydrazine monohydrate (4.9 mL, 100 mmol) were added to a solution of 3-nitroanisole (7.7 g, 50 mmol) in tetrahydrofuran-ethanol solution (1:1, 100 mL), stirred for 3 hours at room temperature, and let stand overnight at about 5° C. The whole was filtered with celite with ethanol (100 mL), and the filtrate was concentrated under reduced pressure. Sodium hydrogen carbonate (13 g, 150 mmol) and anhydrous N,N-dimethylformamide (50 mL) were added to the obtained residue. Moreover under ice-cooling, acetyl chloride (5.4 mL, 76 mmol) was added thereto and the mixture was stirred for 1 hour. The reaction solution was diluted with water (200 mL) and extracted with ethyl acetate (300 mL×1, 200 mL×1). The combined organic layer was washed with brine (100 mL×2) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatograpy to give the title reference compound (9.3 g) as an orange oil (quantitative yield)

1. temperatureUnder ice-cooling
2. waitlet stand overnight at about 5° C
3. filtrationThe whole was filtered with celite with ethanol (100 mL)
4. concentrationthe filtrate was concentrated under reduced pressure
5. temperatureMoreover under ice-cooling
6. stirringthe mixture was stirred for 1 hour
7. extractionextracted with ethyl acetate (300 mL×1, 200 mL×1)
8. washThe combined organic layer was washed with brine (100 mL×2)
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was removed under reduced pressure
11. customthe residue was purified by silica gel column chromatograpy

ORD record

ord-da99cf18538f4b3f822e0210aabaf2da

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445529B2