Water → 1-Methyl-2-(4-nitrobenzylidene)pyrrolidine

HRID 1278044Notes

Reaction equation

HRID 1278044 reaction equation
COS([O-])(=O)=O.CN(C)[C:9]1[CH2:13][CH2:12][CH2:11][N+:10]=1[CH3:14].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].O>C(O)(C)(C)C.CN(C)C=O>[CH3:14][N:10]1[CH2:11][CH2:12][CH2:13][C:9]1=[CH:25][C:22]1[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 74734-NitrotolueneHCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

Product 1

HCID 542294271-Methyl-2-(4-nitrobenzylidene)pyrrolidineYield 22.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Add a solution of 2.35 g of potassium tert. butylate in 15 ml of tert. butanol and 10 ml of dimethylformamide dropwise at 130° to a mixture of 5.0 g of 2-dimethylamino-1-methyl-1-pyrrolinium methylsulfate and 2.2 g of 4-nitrotoluene in 15 ml of dimethylformamide. Stir the thus-prepared reaction mixture at this temperature for 2 hours. Allow the mixture to cool, add water to it and then extract it several times with chloroform. Combine and then concentrate the chloroform extracts. Distil off a slight excess of 4-nitrotoluene under a high vacuum and recrystallize the produced residue from 10 ml of ethanol to obtain 0.8 g of title compound.

Workup

  1. customthe thus-prepared reaction mixture at this temperature for 2 hours
  2. temperatureAllow the mixture to cool
  3. extractionextract it several times with chloroform
  4. concentrationCombine and then concentrate the chloroform
  5. customDistil off a slight excess of 4-nitrotoluene under a high vacuum
  6. customrecrystallize the produced residue from 10 ml of ethanol

Sources & evidence

ORD record
ord-76fd1ac089fd4eb89f31b41fb25acaf2
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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