2-Nitroaniline → Diethyl 2-((2-nitrophenylamino)methylene)malonate

HRID 1743289Notes

Reaction equation

HRID 1743289 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C1(=O)O[CH:16]([O:17]C(C)(C)C)[O:15][C:13](=O)[CH2:12]1.[CH3:24]CCCCC.[C:30]([O:33][CH2:34][CH3:35])(=[O:32])[CH3:31]>>[CH2:34]([O:33][C:30](=[O:32])[C:31](=[CH:24][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])[C:16]([O:15][CH2:13][CH3:12])=[O:17])[CH3:35]

Participants

4

Reactant 3

HCID 69462-NitroanilineHCID 21226206Ethyl acetate hexaneHCID 131725376Dimethylethoxymethylene malonate

Product 1

HCID 225911Diethyl 2-((2-nitrophenylamino)methylene)malonateYield 69%

Conditions

Temperature
120 °C

Procedure

To a solution of 2-nitroaniline (20 g, 144.8 mmol) dissolved in 400 ml of dry-ethanol in a 500 ml round bottom flask was added dimethylethoxymethylene malonate (34 g, 159.3 mmol). The solution was heated and refluxed for 6 hrs at 120° C. with stirring. The reaction was monitered by TLC (n-hexane/ethyl acetate=3/1). After completing the reaction and cooling to room temperature, the resulting precipate was collected by filtration, and the residue was washed three times with 100 ml of n-hexane to give 2-[(2-Nitro-phenylamino)-methylene]-malonic acid diethyl ester (31 g, 100.6 mmol, yield 69%).

Workup

  1. dry with materialof dry-ethanol in a 500 ml round bottom flask
  2. temperatureThe solution was heated
  3. customthe reaction
  4. temperaturecooling to room temperature
  5. filtrationthe resulting precipate was collected by filtration
  6. washthe residue was washed three times with 100 ml of n-hexane

Sources & evidence

ORD record
ord-69e644b92f674661bbbafc812aadb49b
Source dataset
uspto-grants-2006_03
Patent number
US07009053B2

Reaction notes

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