3-(4-Choro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1h, 3h)-pyrimidinedione → 3-(2-amino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([N+:21]([O-])=O)[CH:3]=1>CO.Cl.[Fe]>[NH2:21][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]1=[O:20]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirred suspension of 3-(4-chloro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (1 g) in methanol (20 ml) and conc. hydrochloric acid (10 ml) was added iron (powdered, 0.48 g) unded vigorous stirring. After addition, the mixture was heated at reflux temperature for 1 hr. The oil bath was removed and the solution was allowed to cool to ambient temperature. Ethyl acetate (200 ml) was added, washed with brine (×2) and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was purified by column chromatography on silica gel using ethyl acetate-hexane (1:3) as the eluent to give the title compound.
Workup
- additionAfter addition
- temperaturethe mixture was heated
- temperatureat reflux temperature for 1 hr
- customThe oil bath was removed
- additionEthyl acetate (200 ml) was added
- washwashed with brine (×2)
- dry with materialdried over anhydrous sodium sulfate
- customAfter removal of the solvent
- customthe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-57cd0ed70db949558cde757a6b1b89c9
- Source dataset
- uspto-grants-2007_04
- Patent number
- USRE039590E1
Reaction notes
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