2,4-Dinitrotoluene → 2-(2,4-Dinitrobenzylidene)-1-methylpyrrolidine

HRID 1278085Notes

Reaction equation

HRID 1278085 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH3:13])([O-:3])=[O:2].C(O[C:17]1(OCC)[CH2:21][CH2:20][CH2:19][N:18]1[CH3:22])C>C1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH:13]=[C:17]1[CH2:21][CH2:20][CH2:19][N:18]1[CH3:22])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 84612,4-DinitrotolueneHCID 2973082,2-Diethoxy-1-methylpyrrolidine

Product 1

HCID 14238142-(2,4-Dinitrobenzylidene)-1-methylpyrrolidineYield 34.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Stir 7.0 g of 2,4-dinitrotoluene and 9.65 g of 2,2-diethoxy-1-methylpyrrolidine for 5 hours at 40° in 50 ml of benzene. Allow the resulting reaction mixture to cool to ambient temperature. Filter off the precipitate and wash it with a little benzene and hexane to obtain 3.5 g of the title compound (m.p. 188° to 190°) in the form of black-violet crystals.

Workup

  1. customthe resulting reaction mixture
  2. filtrationFilter off the precipitate
  3. washwash it with a little benzene and hexane

Sources & evidence

ORD record
ord-28c77b591e2546d49576a5cf980a0f53
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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