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

HRID 1913111Notes

Reaction equation

HRID 1913111 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-85de4847ebec470081e2330141a64a29
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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