Diethyl (ethoxymethylene)malonate → Diethyl 2-[(4-methoxy-3-methyl-phenylamino)-methylene]-malonate

HRID 228862

Reaction equation

HRID 228862 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[CH3:10].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][C:4]=1[CH3:10]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 672973-Methyl-4-methoxybenzenamine

Product 1

HCID 12369041Diethyl 2-[(4-methoxy-3-methyl-phenylamino)-methylene]-malonateYield 76%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Methoxy-3-methylaniline (45.2 g) was dissolved in isopropanol (100 ml) to prepare a solution. Diethyl ethoxymethylenemalonate (71.3 g) was added to the solution, and the mixture was heated under reflux for 5 min. The reaction solution was cooled, and the solvent was then removed by distillation under the reduced pressure. The residue was washed with ether-hexane to give diethyl 2-[(4-methoxy-3-methyl-phenylamino)-methylene]-malonate (76.9 g, yield 76%).

Workup

  1. customto prepare a solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 min
  4. temperatureThe reaction solution was cooled
  5. customthe solvent was then removed by distillation under the reduced pressure
  6. washThe residue was washed with ether-hexane

Sources & evidence

ORD record
ord-0f8a561a03784fc2a29306338808346c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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