4-Acetylpyridine → 4-Acetylpyridine-N-oxide

The 3-dimethylamino-1-(1-oxopyrid-4-yl)-2-propen-1-one used as starting material was prepared by heating a solution of 4-acetylpyridine-N-oxide (2.5 g, 18.2 mmol) in dimethylformamide diethylacetal (30 ml) at reflux for 0.5 h. On cooling the resulting solid was collected and washed with diethyl ether to give the desired product (3.18 g) as an orange solid m.p. 181°. The 4-acetylpyridine-N-oxide was prepared by treating a solution of 4-acetylpyridine (3.0 g, 24.8 mmol) in CH2Cl2 with 3-chloro-peroxybenzoic acid [Aldrich 57-86%] (8.4 g) at room temperature for 12 h. The reaction was filtered, the filtrate concentrated under reduced pressure and the resulting residue subjected to column chromatography [silica 10% methanol-ethyl acetate] to give the desired product (3.2 g) as a white solid m.p. 101°.

1. filtrationThe reaction was filtered
2. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-3d75c7f330f84481b7f3662b8ee9a075

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235746B1