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

Reaction equation

HRID 527130 reaction equation
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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-636090814dc841c0bdc11ee7db9a4840
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Linked notes

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