Diethyl (ethoxymethylene)malonate → Diethyl 2-((4-iodophenylamino)methylene)malonate
Reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C(O)C>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[CH:12][NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-iodoaniline (50 g, 0.23 mol) and diethyl ethoxymethylenemalonate (50.3 g, 0.23 mmol) was stirred at 90° C. for 10 hours. 150 mL of ethanol was added and the mixture was refluxed for 3 h. After cooling, the solid was collected, washed with hexane and dried over the oven to obtain 2-[(4-iodo-phenylamino)-methylene]-malonic acid diethyl ester (81 g, 91%) as a white solid.