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-be00d624542341b28593406c166b47c8
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04736037

Reaction notes

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