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

HRID 1930200Notes

Reaction equation

HRID 1930200 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 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

  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 MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-99906488c5294751a1c750559f68a7eb
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

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