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

HRID 2289816Notes

Reaction equation

HRID 2289816 reaction equation
[Cl:1]C1C2C(=CC=C(C(Cl)=O)C=2)C(Cl)=CN=1.ClN1C(=O)CCC1=O.[Br:24][C:25]1[CH:34]=[C:33]2[C:28]([CH:29]=[CH:30][NH:31][C:32]2=[O:35])=[CH:27][CH:26]=1>CC#N>[Br:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([Cl:1])=[CH:30][NH:31][C:32]2=[O:35])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 112761337-Bromoisoquinolin-1-olHCID 186981881,4-Dichloro-7-isoquinolinecarbonyl chloride

Product 1

HCID 211924357-Bromo-4-chloroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1,4-Dichloro-7-isoquinolinecarbonyl chloride ##STR166## 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-e8a071c6774743018a39365d41b115dd
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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