Chlorosuccinimide → 3-(4-Chloro-1-oxo-1,2-dihydroisoquinolin-7-YL)benzonitrile

HRID 479564Notes

Reaction equation

HRID 479564 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([C:11]1[CH:12]=[C:13]([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[CH:22][NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)#[N:10]>CC(N(C)C)=O>[Cl:1][C:21]1[C:20]2[C:25](=[CH:26][C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:9]#[N:10])[CH:12]=3)=[CH:18][CH:19]=2)[C:24](=[O:27])[NH:23][CH:22]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 534249783-(1,2-Dihydro-1-oxo-7-isoquinolinyl)-benzonitrile

Product 1

HCID 534397463-(4-Chloro-1-oxo-1,2-dihydroisoquinolin-7-YL)benzonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of N-chlorosuccinimide (307 g, 2.3 mol) in DMA (1.2 L) was added to a stirred suspension of 7-(3-cyanophenyl)isoquinolinone (0.54 kg, 2.2 mol) in boiling DMA (3.9 L) over a period of 1 hour under N2. The mixture was heated at reflux overnight and cooled to room temperature. The solid was collected by filtration, washed with MeCN (1.0 L) and dried in vacuo at 50° C. to give 4-chloro-7-(3-cyanophenyl)isoquinolinone (0.5 kg, 1.78 mol, 81%) as an off white solid.

Workup

  1. customof 1 hour
  2. temperatureThe mixture was heated
  3. temperatureat reflux overnight
  4. filtrationThe solid was collected by filtration
  5. washwashed with MeCN (1.0 L)
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-2251e72a3633402fbe7564ef110acbcc
Source dataset
uspto-grants-2003_11
Patent number
US06645979B2

Reaction notes

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