Phosphorus oxychloride → 1,7-Dichloro-6-fluoroisoquinoline

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-])=[CH:9]2)=[CH:4][C:3]=1[F:13].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:9]1[C:10]2[C:5](=[CH:4][C:3]([F:13])=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 598182547-Chloro-6-fluoro-isoquinoline 2-oxide

Product 1

HCID 598182461,7-Dichloro-6-fluoroisoquinoline

Procedure

2.6 g (12.0 mmol) of 7-Chloro-6-fluoro-isoquinoline 2-oxide (57) were heated in 40 ml of POCl3 at reflux for 4 h. After the mixture has cooled down to room temperature, it was poured on ice. The aqueous solution was extracted three times with dichloromethane. The combined organic layers were dried with MgSO4 and evaporated to yield 2.91 g of the title compound, which was used without further purification. Rt=2.34 min (Method A). Detected mass: 216.0/218.0 (M+H+).

Workup

temperatureat reflux for 4 h
additionit was poured on ice
extractionThe aqueous solution was extracted three times with dichloromethane
dry with materialThe combined organic layers were dried with MgSO4
customevaporated

Sources & evidence

ORD record: ord-c984dbe8ca4f42759c4437d140df4450
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772492B2

Reaction notes

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