Ethyl 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoate → Ethyl 3-[(2,6-diaminophenyl)amino]-2,2-difluoropropanoate
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH:13][CH2:14][C:15]([F:22])([F:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])([O-])=O>O1CCCC1.[Pd]>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[C:5]=1[NH:13][CH2:14][C:15]([F:21])([F:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]Participants
4
Procedure
To a solution of ethyl 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoate (2.44 g, 7.644 mmol) in tetrahydrofuran (50 mL) was added 10% palladium on carbon (50% wet; 588.0 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 16 hrs. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound as a pale yellow oil (2.00 g, 7.715 mmol, quant.).