Phosphorus oxychloride → 2,5-Dichloropyridin-3-Ol

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5](O)=[N:6][CH:7]=1.P(Cl)(Cl)([Cl:12])=O>>[Cl:12][C:5]1[C:4]([OH:9])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178516188HCID 178516188, compound

Product 1

HCID 98989172,5-Dichloropyridin-3-Ol

Conditions

Temperature: 180 °C

Procedure

A mixture of 5-chloro-2,3-dihydroxypyridine (1.0g.) and phosphoryl chloride (10ml.) was heated overnight at 180°C. in a sealed tube. The phosphoryl chloride was distilled off, and the residue was chromatographed, to give 2,5-dichloro-3-hydroxypyridine, m.p. 160°-161°C. (ethyl acetate - petrol).

Workup

distillationThe phosphoryl chloride was distilled off
customthe residue was chromatographed

Sources & evidence

ORD record: ord-63b1438ab49a4dbfb9b10952623357a6
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03931206

Reaction notes

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