Sulfuric Acid → 1-(4-Chlorobenzoyl)-isoquinoline

HRID 904620Notes

Reaction equation

HRID 904620 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1)#N.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1.[Mg].[Cl-].[NH4+].S(=O)(=O)(O)[OH:25]>CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:1]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][N:4]=2)=[O:25])=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 3060571-IsoquinolinecarbonitrileHCID 5462224Magnesium

Product 1

HCID 122431051-(4-Chlorobenzoyl)-isoquinolineYield 76.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  1. additionis added
  2. waitto stand for a night
  3. customAfter neutralization the ether phase is separated
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-8c72d0a84785403784d252bf197141ff
Source dataset
uspto-grants-1983_12
Patent number
US04419355

Reaction notes

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