Ammonia → 1-Phenylisoquinoline-5-acetonitrile

HRID 1156906Notes

Reaction equation

HRID 1156906 reaction equation
[Na].N.[C:3]1([C:9]2[C:18]3[C:13](=[C:14](Cl)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:20](#[N:22])[CH3:21]>[Fe](Cl)(Cl)Cl>[C:3]1([C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:21][C:20]#[N:22])[C:13]=3[CH:12]=[CH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 6342AcetonitrileHCID 5360545SodiumHCID 128518471-Phenyl-5-chloroisoquinoline

Product 1

HCID 205339011-Phenylisoquinoline-5-acetonitrile

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Procedure

Metallic sodium (1.15 g) was added to 100 ml of liquid ammonia, and 1.3 g of acetonitrile and 2.39 g of 1-phenyl-5-chloroisoquinoline were added to the solution. A small amount of iron trichloride was added, and the reaction was performed for 5 hours. After the reaction, ammonia was distilled off, and ice water was carefully added to the residue. The resulting oily product was extracted with ether, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was chromatographed to afford 1-phenylisoquinoline-5-acetonitrile as an oil.

Workup

  1. additionwere added to the solution
  2. distillationwas distilled off
  3. additionice water was carefully added to the residue
  4. extractionThe resulting oily product was extracted with ether
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was chromatographed

Sources & evidence

ORD record
ord-b1ecab48abdb44b48aa9f4814e16224f
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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