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-4c744984c59f41a3baa65898bb9ae4f9

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07425634B2