Methanol → 3-(4-Cyanobenzylidene)-2-pyrrolidone

HRID 129087Notes

Reaction equation

HRID 129087 reaction equation
C([N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])(=O)C.[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[N:11].[H-].[Na+].CO>O1CCCC1.C(O)(=O)C>[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[C:6]2[CH2:7][CH2:8][NH:4][C:5]2=[O:9])=[CH:14][CH:13]=1)#[N:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydride2×HCID 660424-CyanobenzaldehydeHCID 702662-Pyrrolidinone, 1-acetyl-

Product 1

HCID 538047323-(4-Cyanobenzylidene)-2-pyrrolidoneYield 18%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5.0 g of N-acetyl-2-pyrrolidone and 5.17 g of 4-cyanobenzaldehyde in 50 ml of tetrahydrofuran is added dropwise to a suspension of 5.36 g of sodium hydride (55% in oil) in 50 ml of tetrahydrofuran at 5°-10° C. and the mixture is then stirred at 0° C. for 1 hour. Excess sodium hydride is eliminated by the addition of some methanol, and the reaction mixture is poured onto ice and neutralized with glacial acetic acid. The precipitate is suction-filtered and dissolved in a methylene chloride/methanol mixture, and the solution is dried and evaporated down. The residue is triturated with ether and suction-filtered. 1.4 g of 3-(4-cyanobenzylidene)-2-pyrrolidone are obtained as a colourless powder of melting point 260° C.

Workup

  1. filtrationThe precipitate is suction-filtered
  2. dissolutiondissolved in a methylene chloride/methanol mixture
  3. customthe solution is dried
  4. customevaporated down
  5. customThe residue is triturated with ether
  6. filtrationsuction-filtered

Sources & evidence

ORD record
ord-277b538bf3c74864a9fcdedd20184762
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

Loading…