Ninhydrin → HCID 71477901, compound

HRID 527162Notes

Reaction equation

HRID 527162 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[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])[CH2:11][CH2:12][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 835502HCID 835502, compound

Product 1

HCID 71477901HCID 71477901, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(3,4-dimethylphenyl)butyramide (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 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 silica gel column chromatography (30% ethylacetate in hexane) to afford the title compound (yellow solid, 1.10 g, 56%).

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-9ce8830936d849c6978d96f18e663586
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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