Trifluoroacetic acid → 2-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione

HRID 527126Notes

Reaction equation

HRID 527126 reaction equation
O[C:2]1([OH:16])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[C:3]1=[O:15].[CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1OC)([CH3:19])[CH3:18].[C:28](O)(C(F)(F)F)=[O:29]>>[OH:16][C:2]1([C:23]2[CH:22]=[CH:21][C:20]([CH:17]([CH3:18])[CH3:19])=[CH:25][C:24]=2[O:29][CH3:28])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[C:3]1=[O:15]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1577121H-Indene-1,3(2H)-dione, 2,2-dihydroxy-4-nitro-HCID 2706232-Isopropylanisole

Product 1

HCID 714769702-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dioneYield 16%

Conditions

Temperature
60 °C

Procedure

A solution of 4-nitro-2,3-dihydro-1H-inden-1-one (4.00 g, 20.9 mmol) in 1,4-dioxane (40 ml) and glacial acetic acid (4 ml) was added with selenium dioxide (5.10 g, 46.03 mmol), and refluxed for 3 hrs. After filtration at high temperature, the filtrate was concentrated to afford 2,2-dihydroxy-4-nitro-2H-inden-1,3-dione (4.67 g, 100%). To a solution of 2,2-dihydoxy-4-nitro-2H-inden-1,3-dione (4.67 g, 20.9 mmol) in TFA (10 ml) was added isopropyl anisole (3.14 g, 20.9 mmol), followed by stirring at 60° C. for 6 hrs. The reaction mixture was concentrated in a vacuum, and extracted with aq. sodium bicarbonate and ethylacetate. The concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (1.19 mg, 16%).

Workup

  1. concentrationThe reaction mixture was concentrated in a vacuum
  2. extractionextracted with aq. sodium bicarbonate and ethylacetate
  3. customThe concentrated organic layer was purified

Sources & evidence

ORD record
ord-8e1f3d5d2bff4d91a38439481b17143a
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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