Dichloromethane → HCID 22462459, compound

HRID 1937004Notes

Reaction equation

HRID 1937004 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][CH2:14][CH2:15][CH:5]3[C:4]=2[CH:3]=1.[Cu][C:17]#[N:18].ClCCl>CN(C=O)C>[C:17]([C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][CH2:14][CH2:15][CH:5]3[C:4]=2[CH:3]=1)#[N:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22052537HCID 22052537, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22462459HCID 22462459, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-bromo-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one (230 mg, 0.86 mmol) in DMF (20 ml) is mixed with copper(I) cyanide (77 mg, 0.86 mmol) and refluxed for 16 hours. The batch is diluted dichloromethane, washed with saturated NH4Cl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Purification on silica gel with ethyl acetate-hexane yields 70 mg (38%) of product.

Workup

  1. temperaturerefluxed for 16 hours
  2. washwashed with saturated NH4Cl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum
  5. customPurification on silica gel with ethyl acetate-hexane

Sources & evidence

ORD record
ord-d3311b65f24e4ec78984cfebd21e97e7
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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