Ninhydrin → N-(2-(2-Hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)isobutyramide

HRID 527163Notes

Reaction equation

HRID 527163 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:15]1[CH:20]=[C:19]2[C:21]([C:23](O)([OH:26])[C:24](=[O:25])[C:18]2=[CH:17][CH:16]=1)=[O:22]>S(=O)(=O)(O)O>[OH:26][C:23]1([C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=2[NH:9][C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])[C:24](=[O:25])[C:18]2[C:19](=[CH:20][CH:15]=[CH:16][CH:17]=2)[C:21]1=[O:22]

Participants

4

Reactant 2

HCID 10236NinhydrinHCID 697389N-(3,4-dimethylphenyl)-2-methylpropanamide

Product 1

HCID 71477902N-(2-(2-Hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)isobutyramideYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(3,4-dimethylphenyl)isobutyramide (1.00 mg, 5.61 mmol) and ninhydrin (1.07 mg, 5.61 mmol) were dissolved in conc. sulfuric acid (15 mL) and stirred at room temperature for 5 hrs. The reaction was stopped by slowing pouring the solution to 200 g of ice and stirring. The reaction mixture was extracted with ethylacetate and water, washed with brine. The washed organic layer was dried over sodium sulfate, concentrated in a vacuum, and purified through silica gel column chromatography (30% ethylacetate in hexane) to afford the title compound (yellow solid, 1.85 g, 94%).

Workup

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

Sources & evidence

ORD record
ord-9f67829d23fe4c0aa44a6115adb66d26
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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