2-Bromopropane → 1-Cyano-1-isopropyl-2-benzoyl-1,2-dihydroisoquinoline

HRID 1156907Notes

Reaction equation

HRID 1156907 reaction equation
[C:1]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]1[C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:2].[OH-].[Na+].[CH:23](Br)([CH3:25])[CH3:24]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([C:3]1([CH:23]([CH3:25])[CH3:24])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]1[C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:2]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 2304882-Benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile

Product 1

HCID 125478791-Cyano-1-isopropyl-2-benzoyl-1,2-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

(a-1-1) A mixture of 26 g of 1-cyano-2-benzoyl-1,2-dihydroisoquinoline [Org. Synth. Coll. vol. 4, 641 (1963)] and 1 g of benzyl triethyl ammonium chloride was dissolved in 50 ml of isopropyl bromide. Then, 80 g of a 50% aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 30 minutes. The product was extracted with benzene. The solvent was distilled off, and the residue was recrystallized from ethanol to afford 20 g of 1-cyano-1-isopropyl-2-benzoyl-1,2-dihydroisoquinoline as colorless scales having a melting point of 123.8° to 126.0° C.

Workup

  1. extractionThe product was extracted with benzene
  2. distillationThe solvent was distilled off
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ab2c96cdcf824c0bb900296f6c9d87e7
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…