Benzoyl chloride → HCID 12851876, compound

HRID 1156913Notes

Reaction equation

HRID 1156913 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)#[N:2].[C-:14]#[N:15].[K+].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl.O>[C:14]([CH:9]1[C:10]2[C:5](=[C:4]([CH2:3][C:1]#[N:2])[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][N:8]1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[N:15]

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 128327715-Isoquinolineacetonitrile

Product 1

HCID 12851876HCID 12851876, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Cyanomethylisoquinoline (4.9 g), 5.7 g of potassium cyanide and 200 mg of benzyl triethyl ammonium chloride were dissolved in 60 ml of dichloromethane and 12 ml of water. The solution was stirred for 30 minutes, and 8.2 g of benzoyl chloride was added dropwise. The mixture was further stirred for 4 hours. After the reaction, the dichloromethane layer was washed in water, and dried, followed by distilling off the solvent. The residue was recrystallized from ether to afford 4.5 g of 1-cyano-2-benzoyl-5-cyanomethyl-1,2-dihydroisoquinoline as colorless prisms having a melting point of 66.4° to 69.7° C.

Workup

  1. stirringThe mixture was further stirred for 4 hours
  2. customAfter the reaction
  3. washthe dichloromethane layer was washed in water
  4. customdried
  5. distillationby distilling off the solvent
  6. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-4532c65c2e22444e9a7376f8f8cfa469
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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