Aniline → Malonanilide
Reaction equation
[C:1]1(=[O:6])O[C:3](=[O:4])[CH2:2]1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][C:3]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]Participants
3
Procedure
To the cold solution of malonic anhydride, prepared as above, was added aniline (700 μl, 6 equivalents). The reaction mixture was allowed to warm to room temperature. It was then extracted with 5 ml saturated aqueous NaHCO3, and the aqueous extract was washed with 5 ml ether, acidified with H2SO4, and extracted with 3 4-ml portions of ether. The ether extracts were combined and dried over Na2SO4, and the ether was removed under reduced pressure, to leave a residue of malonanilide (mp 127°-130° C., 180 mg, 72% isolated yield, based on diketene).
Workup
- extractionIt was then extracted with 5 ml saturated aqueous NaHCO3
- extractionthe aqueous extract
- washwas washed with 5 ml ether
- extractionextracted with 3 4-ml portions of ether