p-Nitrophenylacetonitrile → 2-(alpha-Cyano-4-nitrobenzylidene)-1-methylpyrrolidine

HRID 1278074Notes

Reaction equation

HRID 1278074 reaction equation
C(O[C:4]1(OCC)[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9])C.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1C=CC=CC=1>[C:23]([C:22](=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9])[C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=1)#[N:24]

Participants

4

Reactant 2

HCID 68386p-NitrophenylacetonitrileHCID 2973082,2-Diethoxy-1-methylpyrrolidine

Product 1

HCID 544376362-(alpha-Cyano-4-nitrobenzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Stir 29.9 g of 2,2-diethoxy-1-methylpyrrolidine and 28 g of 4-nitrophenylacetonitrile in 80 ml of benzene for one hour at room temperature. Distil off the solvent from the resulting reaction mixture under a vacuum to produce a crystalline residue. Recrystallize this residue from ethanol/diethyl ether. Concentrate the mother liquor to obtain a total of 29.5 g (70% of theory) of the title compound as dark-brown shiny crystals of m.p. 67°.

Workup

  1. customDistil off the solvent
  2. customfrom the resulting reaction mixture under a vacuum
  3. customto produce a crystalline residue
  4. customRecrystallize this residue from ethanol/diethyl ether
  5. concentrationConcentrate the mother liquor

Sources & evidence

ORD record
ord-2286baadb1cf47f48bddfcc51e136d07
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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