Phosphorus oxychloride → 5-Bromo-1-chloroisoquinoline

HRID 2356363Notes

Reaction equation

HRID 2356363 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N+:6]([O-])=[CH:7]2.P(Cl)(Cl)([Cl:15])=O>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[Cl:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22665708Isoquinoline, 5-bromo-, 2-oxide

Product 1

HCID 211924975-Bromo-1-chloroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromoisoquinoline-N-oxide (4.56 g, 20.4 mmol) in 100 mL CH2Cl2, phosphorus oxychloride (4.17 ml, 44.8 mmol) was added and the mixture heated at 45 C for 4 h. The mixture was allowed to cool and evaporated. Water and ice were added alternating, portion-wise and CH2Cl2 was added to the mixture. The organic layer was made pH 14 with 1 M NaOH, and the organic layer washed with sat. NaHCO3, dried over Na2SO4, filtered and evaporated. The solid was triturated with methanol and the title compound collected as a fluffy off-white solid (3.93 g). MS (ESI pos. ion) m/z: 242 (MH+). Calc'd exact mass for C9H5BrClN: 242.

Workup

  1. temperaturethe mixture heated at 45 C for 4 h
  2. temperatureto cool
  3. customevaporated
  4. additionWater and ice were added
  5. additionportion-wise and CH2Cl2 was added to the mixture
  6. washthe organic layer washed with sat. NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid was triturated with methanol
  11. customthe title compound collected as a fluffy off-white solid (3.93 g)

Sources & evidence

ORD record
ord-dc009e2cda45420d87ebf9609b83ce3f
Source dataset
uspto-grants-2010_07
Patent number
US07759344B2

Reaction notes

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