HCID 13245209, compound → 4-(1-Benzofuran-2-yl)pyrrolidin-2-one

HRID 325937Notes

Reaction equation

HRID 325937 reaction equation
[N+:1]([CH2:4][CH:5]([C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[CH:16]=1)[CH2:6][C:7](OCC)=[O:8])([O-])=O.[H][H]>C(O)C.[Ni]>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[CH:16]=[C:12]1[CH:5]1[CH2:4][NH:1][C:7](=[O:8])[CH2:6]1

Participants

5

Reactant 2

HCID 13245209HCID 13245209, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 132452104-(1-Benzofuran-2-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Ester (IV) (81.5 g; 0.297 mole) obtained in b) is dissolved in 500 ml ethanol and hydrogenated at ordinary pressure at 55° C. in the presence of 10 g Raney Nickel. The hydrogen required for the reaction (14.8 l) is taken up within 7 hours. After filtration of the catalyst and evaporation of the ethanol, the oily residue is heated at 100° C. under the vacuum of a water pump, for 2 hours. On trituration with isopropyl ether, the product crystallizes. M.P. (inst.)=142° C. Weight: 47.9 g (80%).

Workup

  1. filtrationAfter filtration of the catalyst and evaporation of the ethanol
  2. customOn trituration with isopropyl ether, the product crystallizes
  3. customM.P. (inst.)=142° C

Sources & evidence

ORD record
ord-04b6d473e8804569bbf3ecfb4abc1306
Source dataset
uspto-grants-1984_04
Patent number
US04443468

Reaction notes

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