Water → 3-(3-Chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 1033160노트

반응식

HRID 1033160 반응식
[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]

참가 물질

5

반응물 2

HCID 962WaterHCID 19025375methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate

생성물 1

HCID 190253833-(3-Chloro-6-fluoro-3,4-dihydroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil수율 221.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  1. customThis compound was prepared in a manner analogous to that of Step D of this Example
  2. customfrom another run (0.014 mole) of this reaction
  3. washElution
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-79346ff66d8c465b86a676bbb2e69355
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310723

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