Diethyl (ethoxymethylene)malonate → 2-((4-Methoxy-phenylamino)-methylene)-malonic acid diethyl ester

HRID 638966Notes

Reaction equation

HRID 638966 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>CCO>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[CH:13][NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:19]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7732P-Anisidine

Product 1

HCID 6189812-((4-Methoxy-phenylamino)-methylene)-malonic acid diethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-aminoanisole (50 g, 0.406 mol) in EtOH (500 mL) was added diethyl ethoxymethylenemalonate (81 mL, 0.406 mol). The reaction solution was refluxed for 4 h; LCMS showed complete reaction. The reaction solution was concentrated under reduced pressure to give the desired product (118 g, 100%) as a crystalline solid.

Workup

  1. temperatureThe reaction solution was refluxed for 4 h
  2. customreaction
  3. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d6b2d3467ef4dbbbaa319dd9cf0c2a1
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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