p-Bromochlorobenzene → 3-(4-Chlorobenzoyl)-isoquinoline imine

HRID 904618Notes

Reaction equation

HRID 904618 reaction equation
[Mg].[Cl:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[C:10]([C:12]1[N:13]=[CH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)#[N:11].[Cl-].[NH4+]>CCOCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:10](=[NH:11])[C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 50768083-IsoquinolinecarbonitrileHCID 5462224Magnesium

Product 1

HCID 28256043-(4-Chlorobenzoyl)-isoquinoline imineYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The starting substance is prepared as follows: To a mixture of 0.62 g (26 millimoles) of metallic magnesium and 8 ml of anhydrous ether a solution of 5.0 g (26 millimoles) of 4-chloro-bromobenzene in ether is dropwise added, the Grignard solution thus-obtained is admixed with 3.1 g (20 millimoles) of 3-cyano-isoquinoline, and the reaction mixture is stirred at room temperature for an hour. The Grignard complex is decomposed with an ammonium chloride solution, the solvent is distilled off and the residue is recrystallized from ethanol. 3.2 g (60%) of 3-(4-chlorobenzoyl)-isoquinoline imine are obtained.

Workup

  1. customThe starting substance is prepared
  2. additionis dropwise added
  3. customthe Grignard solution thus-obtained
  4. distillationthe solvent is distilled off
  5. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-a0bc1ef5934a47d78fc695e65761307f
Source dataset
uspto-grants-1983_12
Patent number
US04419355

Reaction notes

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