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

HRID 1067232Notes

Reaction equation

HRID 1067232 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N+:12]([O-])[CH:11]=[CH:10]2>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([Cl:3])=[N:12][CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 222501786-Bromoisoquinoline 2-oxide

Product 1

HCID 222502446-Bromo-1-chloro-isoquinolineYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus oxychloride (0.60 mL, 6.44 mmol) was added in one portion to a stirred solution of 6-bromoisoquinoline N-oxide (409 mg, 1.83 mmol) in CH2Cl2 (10 mL) and the mixture was heated at reflux for 6 hours. Excess solvents were evaporated in vacuo, the residue suspended in water (10 mL) and basified with 0.880 ammonia. This mixture was extracted with CH2Cl2 (2×25 mL) and the combined organics were dried over MgSO4 and evaporated in vacuo to leave the crude product. Purification by column chromatography upon silica gel using hexanes-EtOAc (90:10) as eluant gave 6-bromo-1-chloroisoquinoline (215 mg, 0.86 mmol) as a cream-coloured solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 hours
  3. customExcess solvents were evaporated in vacuo
  4. extractionThis mixture was extracted with CH2Cl2 (2×25 mL)
  5. dry with materialthe combined organics were dried over MgSO4
  6. customevaporated in vacuo
  7. customto leave the crude product
  8. customPurification by column chromatography upon silica gel

Sources & evidence

ORD record
ord-eea1920dc6374e42938df1f81909520d
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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