Acetic Acid → N-(2-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-5-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

HRID 527131

Reaction equation

HRID 527131 reaction equation
O[C:2]1([OH:20])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]=2[NH:12][C:13](=[O:15])[CH3:14])[C:3]1=[O:19].[Se]=O.CC(O)=O.[CH:27]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)([CH3:29])[CH3:28]>O1CCOCC1>[OH:20][C:2]1([C:33]2[CH:34]=[CH:35][C:30]([CH:27]([CH3:29])[CH3:28])=[CH:31][C:32]=2[O:36][CH3:37])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]=2[NH:12][C:13](=[O:15])[CH3:14])[C:3]1=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 167175OxyselenideHCID 109316061-Isopropyl-3-methoxy-benzeneHCID 86717341N-(2,2-dihydroxy-5-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Product 1

HCID 71477131N-(2-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-5-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamideYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(2,2-dihydroxy-5-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (2.60 g, 11.1 mmol) was completely dissolved in anhydrous dioxane (20 ml). This solution was added with selenium oxide (2.70 g, 24.4 mmol) and AcOH (1.5 ml). The reaction mixture was heated for 7 hrs under reflux. After filtration at high temperature, the filtrate was concentrated to afford 1.79 g (100%). Trifluoroacetic solution of the resulting product was added with isopropyl-3-methoxybenzene (1.66 g, 11.1 mmol), followed by stirring for 12 hrs. The remainder was extracted with ethyl acetate, and concentrated organic layer was purified using column chromatography (ethylacetate 100%) to afford the title compound (0.64 g, 14%).

Workup

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

Sources & evidence

ORD record
ord-b9026bf2745a4c489f3604990c375759
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Linked notes

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