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

HRID 402518Notes

Reaction equation

HRID 402518 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 had 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-7cf16209865744ce916f65461ff93d07
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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