2-Bromo-4'-methylacetophenone → HCID 12335292, compound

HRID 248404Notes

Reaction equation

HRID 248404 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=O>CC(C)=O>[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:7]([C:8]#[N:9])=[C:2]3[N:1]([CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3]3)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 75959Pyridine-2-acetonitrile2×

Product 1

HCID 12335292HCID 12335292, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-pyridyl acetonitrile (5.0 g) and 2-bromo-4'-methylacetophenone (8.52 g) in acetone (10 ml) was heated at 80° C. for 24 hours, during which 2-pyridylacetonitrile (1 g, 2 g) was added to the reaction mixture. After being cooled, the solvent was removed in vacuo and the residue was chromatographed on silica gel eluted with a mixture of ethyl acetate and n-hexane (1:6 to 1:2, V/V) to give a solid product. This product was recrystallized from ethanol-water to give 2-(4-methylphenyl)indolizine-1-carbonitrile (4.1 g) as a pale brown powder.

Workup

  1. additionwas added to the reaction mixture
  2. temperatureAfter being cooled
  3. customthe solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel
  5. washeluted with a mixture of ethyl acetate and n-hexane (1:6 to 1:2, V/V)
  6. customto give a solid product
  7. customThis product was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-2638f662365644dd9131cf8b213f8551
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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