Acetyl chloride → HCID 59792475, compound

Temperature

-15 °C

First, 3-ethyl-2-methyl-4-nitropyridine 1-oxide (3.37 g, 18.5 mmol) was added to acetyl chloride (20 ml, 281 mmol) in a nitrogen atmosphere at −30° C. The mixture was stirred at −30 to 0° C. for 3 hours. After the reaction mixture was concentrated, the residue was partitioned by chloroform and a saturated aqueous sodium hydrogen carbonate solution. After insoluble substance was removed by filtration, the aqueous layer was extracted twice with chloroform. The organic layers were combined and dried over anhydrous magnesium sulfate, filtrated and concentrated. The residue was purified by silica gel column chromatography (NH silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate=50/50) to obtain the title compound (2.10 g, yield: 66.1%) as a yellow oil.

1. concentrationAfter the reaction mixture was concentrated
2. customthe residue was partitioned by chloroform
3. customAfter insoluble substance was removed by filtration
4. extractionthe aqueous layer was extracted twice with chloroform
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltrated
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (NH silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate=50/50)

ORD record

ord-426ed23441fd40c59e2b6fa7be030d3c

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124780B2