Phosphorus oxychloride → 6-Bromo-1-chloro-isoquinoline

HRID 404718Notes

Reaction equation

HRID 404718 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N+:7]([O-])[CH:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:15]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:15])=[N:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 222501786-Bromoisoquinoline 2-oxide

Product 1

HCID 222502446-Bromo-1-chloro-isoquinoline

Procedure

53.0 g (236, mmol) of 6-bromo-isoquinoline 2-oxide (4) were heated in 400 ml of POCl3 under reflux conditions in two portions. After 4 h, the reaction was cooled to room temperature and poured carefully on ice with mechanical stirring. The aqueous solution was extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate and evaporated, which gave 42.8 g of the title compound, which was used without further purification. Rt=1.64 min (Method C). Detected mass: 242.1/244.2 (M+H+).

Workup

  1. additionpoured carefully on ice with mechanical stirring
  2. extractionThe aqueous solution was extracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-27a094df04064df4bb8682d15163dd9a
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

Loading…