Water → 3-(3-Chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil
Reaction equation
[Cl:1][CH:2]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[CH:10][C:9]=1[N+:28]([O-])=O)[C:3]([O:5]C)=O.O>C(O)(=O)C.[Fe]>[Cl:1][CH:2]1[CH2:7][C:8]2[C:9](=[CH:10][C:11]([N:15]3[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]3=[O:27])=[C:12]([F:14])[CH:13]=2)[NH:28][C:3]1=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
This compound was prepared in a manner analogous to that of Step D of this Example, using 2.9 grams (0.006 mole) of methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate, 2.0 grams (0.036 g-atom) of iron powder, and 5 mL of water in 50 mL of acetic acid. The product from this reaction was combined with that from another run (0.014 mole) of this reaction. The combination was subjected to column chromatography on silica gel. Elution was accomplished using heptane, 1:1 heptane-ethyl acetate, and ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 5.2 grams of 3-(3-chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil. The NMR spectrum was consistent with the proposed structure.
Workup
- customThis compound was prepared in a manner analogous to that of Step D of this Example
- customfrom another run (0.014 mole) of this reaction
- washElution
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-79346ff66d8c465b86a676bbb2e69355
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05310723
Reaction notes
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