6-Bromoisoquinoline N-oxide hydrochloride → 6-Bromo-1-chloro-isoquinoline

HRID 1279006Notes

Reaction equation

HRID 1279006 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N+:8]([O-])[CH:7]=[CH:6]2>P(Cl)(Cl)(Cl)=O>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([Cl:1])=[N:8][CH:7]=[CH:6]2

Participants

3

Reactant 1

HCID 226656306-Bromoisoquinoline N-oxide hydrochloride

Product 1

HCID 222502446-Bromo-1-chloro-isoquinolineYield 72.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
90 °C

Procedure

70 mL of phosphorylchloride were added to 14.9 g of 1a and the mixture was heated at 90° C. for 2 hours. Excess of phosphorylchloride was evaporated, water was added, followed by aqueous 2N NaOH until pH 9 and the mixture was extracted with dichloromethane. The dichloromethane extract was washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (toluene/ethyl acetate=4/1) giving 10.1 g of 1b. M.p.=102.7-103.7° C.

Workup

  1. customExcess of phosphorylchloride was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with dichloromethane
  4. extractionThe dichloromethane extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel (toluene/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-71499b99ed904bc5bc1ce6f02edba9f7
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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