Water → 4-(2,5-Dihydro-1H-pyrrole-1-carbonyl)-3-methylbenzonitrile

HRID 2053753Notes

Reaction equation

HRID 2053753 reaction equation
[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][C:9]=2[CH3:15])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.[Cu](C#N)[C:17]#[N:18].O.C(OCC)(=O)C>CN(C)C=O>[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:17]#[N:18])=[CH:10][C:9]=2[CH3:15])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 22600480(4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanoneHCID 178418260HCID 178418260, compound

Product 1

HCID 226004824-(2,5-Dihydro-1H-pyrrole-1-carbonyl)-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

31.6 g (0.11 mol) of 4-(2,5-dihydropyrrol-1-ylcarbonyl)-3-methylbromobenzene is dissolved in 125 mL of dimethylformamide and combined with 20.2 g (0.23 mol) of copper cyanide and 3.2 g (2.7 mmol) of tetrakis-triphenylphosphinepalladium(0). The suspension is stirred for 20 hours at 140° C. Then it is cooled to 80° C., combined with 150 mL of water, 150 mL of ethyl acetate, and 25 g of CELITE® filter aid and filtered through CELITE® filter aid. The organic phase is separated off, washed with sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with ethyl acetate/ethanol (50:1 and 19:1). The corresponding fractions are combined and concentrated by evaporation. Yield: 11.7 g (49% of theory); Rf value: 0.55 (silica gel; ethyl acetate/ethanol=9:1).

Workup

  1. temperatureThen it is cooled to 80° C.
  2. filtrationfilter aid
  3. filtrationfiltered through CELITE®
  4. filtrationfilter aid
  5. customThe organic phase is separated off
  6. washwashed with sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed on silica gel
  10. washeluting with ethyl acetate/ethanol (50:1 and 19:1)
  11. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fc94ac9fc4c046f4bf3b57cbbd5699c5
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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