Phosphorus oxychloride → 5-Bromo-1-chloroisoquinoline

HRID 1403074Notes

Reaction equation

HRID 1403074 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N+:11]([O-])=[CH:12]2>C(Cl)(Cl)Cl>[Cl:3][C:12]1[C:13]2[C:8](=[C:7]([Br:6])[CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

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

Product 1

HCID 211924975-Bromo-1-chloroisoquinolineYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Phosphorus oxychloride (5 ml) was added to a suspension of compound (1a) (7.83 g) in chloroform (120 ml), and the mixture was stirred overnight at 50° C. The solvent was distilled off under reduced pressure, and chloroform was added to the residue. The reaction solution was neutralized with an aqueous sodium hydroxide solution with cooling in an ice bath and partitioned into organic and aqueous layers. The organic layer was washed with brine. The organic layer thus washed was dried over anhydrous sodium sulfate. Then, the solvent was distilled off, and small amounts of chloroform and diethyl ether were added to the residue. The deposit was filtrated to obtain compound (1b) (5.83 g, 65%) as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and chloroform
  2. additionwas added to the residue
  3. temperaturewith cooling in an ice bath
  4. custompartitioned into organic and aqueous layers
  5. washThe organic layer was washed with brine
  6. washThe organic layer thus washed
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. additionsmall amounts of chloroform and diethyl ether were added to the residue
  10. filtrationThe deposit was filtrated

Sources & evidence

ORD record
ord-8af9bc456c9f4ad3a27cfa1f3c38d922
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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