Sodium Hydroxide → 7-Bromo-1,3-dichloroisoquinoline

HRID 2060367Notes

Reaction equation

HRID 2060367 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-])=[C:9]2[Cl:12])=[CH:4][CH:3]=1.[OH-].[Na+].O=P(Cl)(Cl)[Cl:18]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([Cl:18])[N:8]=[C:9]2[Cl:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 58128286Isoquinoline, 7-bromo-1-chloro-, 2-oxide

Product 1

HCID 534012027-Bromo-1,3-dichloroisoquinoline

Procedure

7-Bromo-1-chloroisoquinoline 2-oxide (1.43 g, 5.56 mmol) and POCl3 (20 mL) were heated at reflux for 2 h. The reaction mixture was cooled and carefully poured onto a mixture of ice/water (500 g), stirred for 1 h and the pH adjusted to 10.0 with 10M NaOH. The mixture was extracted with chloroform (2×100 mL) and the chloroform extracts washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (1.40 g). LRMS (M+H)+=276.0.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe reaction mixture was cooled
  3. extractionThe mixture was extracted with chloroform (2×100 mL)
  4. washthe chloroform extracts washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd328fa39e7542539dd613b5fa2c0f81
Source dataset
uspto-grants-2012_10
Patent number
US08278322B2

Reaction notes

Loading…