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

HRID 527159Notes

Reaction equation

HRID 527159 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:13]1[CH:18]=[C:17]2[C:19]([C:21](O)([OH:24])[C:22](=[O:23])[C:16]2=[CH:15][CH:14]=1)=[O:20]>S(=O)(=O)(O)O>[OH:24][C:21]1([C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=2[NH:9][C:10](=[O:12])[CH3:11])[C:22](=[O:23])[C:16]2[C:17](=[CH:18][CH:13]=[CH:14][CH:15]=2)[C:19]1=[O:20]

Participants

4

Reactant 2

HCID 10236NinhydrinHCID 751443',4'-Dimethylacetanilide

Product 1

HCID 71477898N-(2-(2-Hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)acetamideYield 44%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(3,4-dimethylphenyl)acetamide (915 mg, 5.62 mmol) and ninhydrin (1.00 g, 5.62 mmol) were dissolved in conc. sulfuric acid (20 mL) and stirred at room temperature for 1.5 hrs. The reaction was stopped by slowing pouring the solution to 150 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 column chromatography (30% ethylacetate in hexane) to afford the title compound (yellow solid, 800 mg, 44%).

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 column chromatography (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-1ee262d141c5442b91b9df91f502ade4
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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