Réaction #991802

ord-8c72d0a84785403784d252bf197141ff

Équation de réaction

O=S(=O)(O)O
sulfuric acid
[Cl-].[NH4+]
ammonium chloride
N#Cc1nccc2ccccc12
1-cyano-isoquinoline
Clc1ccc(Br)cc1
4-chloro-bromobenzene
[Mg]
magnesium
O=C(c1ccc(Cl)cc1)c1nccc2ccccc12
1-(4-chlorobenzoyl)-isoquinoline
Rendement 76.6%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONis added
  2. 2
    workup.WAITto stand for a night
  3. 3
    AutreAfter neutralization the ether phase is separated
  4. 4
    workup.DISTILLATIONthe solvent is distilled off

Mode opératoire

To a solution of 3.1 g (20 millimoles) of 1-cyano-isoquinoline in anhydrous ether a Grignard reagent prepared from 5.75 g (30 millimoles) of 4-chloro-bromobenzene and 0.735 g (30 millimoles) of magnesium metal is added. The reaction mixture is allowed to stand for a night, thereafter the complex is decomposed with ammonium chloride solution, acidified with a 20% sulfuric acid and allowed to stand for 2 hours. After neutralization the ether phase is separated and the solvent is distilled off. 4.1 g (76.6%) of 1-(4-chlorobenzoyl)-isoquinoline are obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04419355uspto-grants-1983_12