Ethyl 4-nitrophenylacetate → 2-(alpha-Ethoxycarbonyl-4-nitrobenzylidene)-1-methylpyrrolidine

HRID 1278043Notes

Reaction equation

HRID 1278043 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].C(O[C:19]1(OCC)[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])C>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5](=[C:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 79517Ethyl 4-nitrophenylacetateHCID 2973082,2-Diethoxy-1-methylpyrrolidine

Product 1

HCID 545197932-(alpha-Ethoxycarbonyl-4-nitrobenzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Boil 50 g of 4-nitrophenylacetic acid ethyl ester and 41.4 g of 2,2-diethoxy-1-methylpyrrolidine under reflux for 3 hours in 250 ml of benzene. Distil off the benzene before recrystallizing the resulting residue from diethyl ether/petroleum ether to obtain the title compound at a yield of 52.6 g (77% of theory) in the form of red crystals of m.p. 82° to 83°.

Workup

  1. customDistil off the benzene
  2. custombefore recrystallizing the resulting residue from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-be52418171e1411985dd9643aa0b5774
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…