Phosphorus oxychloride → (6-Chloro-2-pyridinyl)phenylmethanone

Reaction equation

[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[O-])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:18]>>[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:18])[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 849885(1-Oxido-2-pyridinyl)(phenyl)methanone

Product 1

HCID 14023163(6-Chloro-2-pyridinyl)phenylmethanone

Procedure

1.5 g 2-benzoyl-pyridine N-oxide (T. Kato et. al., see reference in Ex. 11) and 3.6 ml POCl3 are refluxed for 25 minutes. The cooled mixture is added to slightly alkaline ice:water, extracted with chloroform, the organic extract dried and solvent removed in vacuo. Yield: 1.1 g of title product, which by thin layer and gas chromatography is identical with that described in Ex. 7.

Workup

additionThe cooled mixture is added to slightly alkaline ice
extractionwater, extracted with chloroform
extractionthe organic extract
customdried
customsolvent removed in vacuo

Sources & evidence

ORD record: ord-75a734f4b7af4e6c92462028b3194e26
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04614833

Reaction notes

Loading…