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

HRID 2059580Notes

Reaction equation

HRID 2059580 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 (4) 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-fb3ec38cabbc4589a151f2ca6ca6887b
Source dataset
uspto-grants-2012_10
Patent number
US08278294B2

Reaction notes

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