N-(3,4-dimethylphenyl)-2-methylpropanamide → N-(2-(4-Acetamido-2-hydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)isobutyramide

HRID 527166Notes

Reaction equation

HRID 527166 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].[CH3:21][C:22]1[CH:23]=[C:24]([NH:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH:25]=[CH:26][C:27]=1[CH3:28]>S(=O)(=O)(O)O>[C:13]([NH:12][C:8]1[CH:7]=[CH:6][C:5]([N+:16]([O-:18])=[O:17])=[C:4]2[C:9]=1[C:10](=[O:11])[C:2]([C:25]1[CH:26]=[C:27]([CH3:28])[C:22]([CH3:21])=[CH:23][C:24]=1[NH:29][C:30](=[O:34])[CH:31]([CH3:32])[CH3:33])([OH:20])[C:3]2=[O:19])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 697389N-(3,4-dimethylphenyl)-2-methylpropanamideHCID 86717356N-(2,2-dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Product 1

HCID 71478042N-(2-(4-Acetamido-2-hydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)isobutyramideYield 10%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(2,2-dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (0.20 g, 0.71 mmol) and N-(3,4-dimethylphenyl)isobutyramide (136 mg, 0.71 mmol) were dissolved in conc. sulfuric acid (5 mL) and stirred at room temperature for 3 hrs. The reaction mixture was extracted with ethylacetate and ice-water, washed with brine. The washed organic layer dried over sodium sulfate, concentrated in a vacuum, and purified through silica gel column chromatography (30% ethylacetate in hexane) to afford the title compound (30 mg, 10%).

Workup

  1. extractionThe reaction mixture was extracted with ethylacetate and ice-water
  2. washwashed with brine
  3. dry with materialThe washed organic layer dried over sodium sulfate
  4. concentrationconcentrated in a vacuum
  5. custompurified through silica gel column chromatography (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-c7da4daf4770461b932f9e194259997a
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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