Chlorosuccinimide → 7-Bromo-4-chloroisoquinolin-1(2H)-one

HRID 1067245Notes

Reaction equation

HRID 1067245 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][NH:16][C:17]2=[O:20])=[CH:12][CH:11]=1>CC#N>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:1])=[CH:15][NH:16][C:17]2=[O:20])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 112761337-Bromoisoquinolin-1-ol

Product 1

HCID 211924357-Bromo-4-chloroisoquinolin-1(2H)-oneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of N-chlorosuccinimide (4.13 g, 31 mmol) in MeCN (50 mL) was added dropwise to a stirred solution of 7-bromo-1-(2H)-isoquinolone (6.6 g, 29.5 mmol) in MeCN (150 mL) which was heating under reflux. The mixture was heated under reflux for an additional 3 h and then cooled to room temperature. The resulting precipitate was collected by filtration, with MeCN rinsing, and then dried in vacuo to give 7-bromo-4-chloro-1(2H)-isoquinolone (6.72 g, 26.0 mmol) as a white solid.

Workup

  1. temperaturewas heating
  2. temperatureunder reflux
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for an additional 3 h
  5. filtrationThe resulting precipitate was collected by filtration, with MeCN rinsing
  6. customdried in vacuo

Sources & evidence

ORD record
ord-83494b379edd4adbb77ecf8a7158a718
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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