Phosphorus oxychloride → 5-Bromo-1-chloro-6-methoxyisoquinoline

HRID 1436012Notes

Reaction equation

HRID 1436012 reaction equation
O=P(Cl)(Cl)Cl.[ClH:6].[Br:7][C:8]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N+:12]([O-])=[CH:13]2>>[Br:7][C:8]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[C:13]2[Cl:6]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 688780245-bromo-6-methoxyisoquinoline-N-oxide hydrochloride

Product 1

HCID 579564605-Bromo-1-chloro-6-methoxyisoquinolineYield 110.1%

Conditions

Temperature
90 °C

Procedure

POCl3 (6.5 ml) was added to the 5-bromo-6-methoxyisoquinoline-N-oxide hydrochloride (1.22 g) and the mixture heated at 90° C. for 6 h. Excess POCl3 was removed in vacuo and the remaining solid washed with water, filtered and dried in vacuo to give 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g).

Workup

  1. customExcess POCl3 was removed in vacuo
  2. washthe remaining solid washed with water
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f1c98be2325144308728bc9ba854eb7e
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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