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

HRID 2402571Notes

Reaction equation

HRID 2402571 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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 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 (5) 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 magnesium sulfate 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

  1. temperatureat reflux for 4 h
  2. additionit was poured on ice
  3. extractionThe aqueous solution was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-419f693f1ce74c92b8464fc9875d5dc4
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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