Aniline → 3-anilino-4-ethoxycyclobut-3-ene-1,2-dione
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11]1[C:12](=O)[C:13](=[O:18])[C:14]=1[O:15]CC)[CH3:9]>C(O)C>[NH:1]([C:12]1[C:13](=[O:18])[C:14](=[O:15])[C:11]=1[O:10][CH2:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.01 mol of aniline is added to a solution of 0.01 mol of 3,4-diethoxy-3-cyclobutene-1,2-dione in 30 ml of anhydrous ethanol. The mixture is refluxed for 12 hours and the precipitate that forms is filtered off while hot. The resulting residue is solidified in the presence of ether enabling the expected product to be isolated.
Workup
- temperatureThe mixture is refluxed for 12 hours
- filtrationthe precipitate that forms is filtered off while hot
- customto be isolated
Sources & evidence
- ORD record
- ord-40be4c9f7a3141159b528697653cbc94
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696469B2
Reaction notes
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