Dimethyl Sulfoxide → 1-(4-Bromophenyl)isoquinoline-5-acetonitrile

HRID 1156872Notes

Reaction equation

HRID 1156872 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:19](=[C:20]([CH2:25]Cl)[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:25][C:1]#[N:2])[C:19]=3[CH:18]=[CH:17][N:16]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 12851833HCID 12851833, compound

Product 1

HCID 128518341-(4-Bromophenyl)isoquinoline-5-acetonitrileYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2.5 g of sodium cyanide and 150 ml of dimethylsulfoxide was added 14 g of 1-(4-bromophenyl)-5-chloromethylisoquinoline little by little. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a mixture of ethyl acetate and a dilute aqueous solution of sodium bicarbonate. The organic layer was separated, dried, and recrystallized from dichloromethane-hexane to afford 8.5 g of 1-(4-bromophenyl)isoquinoline-5-acetonitrile as colorless prisms having a melting point of 121.5° to 122.5° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customrecrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-6d2ae4387bbb4089b1475f11de3080bd
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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