Trifluoroacetic acid → N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

HRID 527130

반응식

HRID 527130 반응식
O[C:2]1([OH:20])[C:10](=[O:11])[C:9]2[C:4](=[C:5]([N+:16]([O-:18])=[O:17])[CH:6]=[CH:7][C:8]=2[NH:12][C:13](=[O:15])[CH3:14])[C:3]1=[O:19].[Se]=O.FC(F)(F)C(O)=O.[CH:30]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=1)([CH3:32])[CH3:31]>O1CCOCC1.CC(O)=O>[OH:20][C:2]1([C:36]2[CH:37]=[CH:38][C:33]([CH:30]([CH3:32])[CH3:31])=[CH:34][C:35]=2[O:39][CH3:40])[C:10](=[O:11])[C:9]2[C:4](=[C:5]([N+:16]([O-:18])=[O:17])[CH:6]=[CH:7][C:8]=2[NH:12][C:13](=[O:15])[CH3:14])[C:3]1=[O:19]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 167175OxyselenideHCID 109316061-Isopropyl-3-methoxy-benzeneHCID 86717356N-(2,2-dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

생성물 1

HCID 71476974N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide수율 20%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 312751,4-Dioxane용매

실험 절차

N-(2,2-dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (1.50 g, 6.4 mmol) was completely dissolved in anhydrous dioxane (15 ml). This solution was added with selenium oxide (1.56 g, 14.0 mmol) and AcOH (1.5 ml). The reaction mixture was heated for 12 hrs under reflux. After filtration at high temperature, the filtrate was concentrated to afford 1.79 g (100%). A trifluoroacetic acid solution of the resulting product was added with isopropyl-3-methoxy benzene (962 mg, 6.4 mmol) followed by stirring for 12 hours. The resulting product was extracted with ethyl acetate, and concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:1) to afford the title compound (0.52 g, 20%).

후처리

  1. temperatureThe reaction mixture was heated for 12 hrs
  2. temperatureunder reflux
  3. filtrationAfter filtration at high temperature
  4. concentrationthe filtrate was concentrated
  5. customto afford 1.79 g (100%)
  6. extractionThe resulting product was extracted with ethyl acetate, and concentrated organic layer
  7. customwas purified

출처 및 근거

ORD 기록
ord-636090814dc841c0bdc11ee7db9a4840
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346749B2

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