Ninhydrin → HCID 71477899, compound

HRID 527160Notes

Reaction equation

HRID 527160 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:14]1[CH:19]=[C:18]2[C:20]([C:22](O)([OH:25])[C:23](=[O:24])[C:17]2=[CH:16][CH:15]=1)=[O:21]>S(=O)(=O)(O)O>[OH:25][C:22]1([C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=2[NH:9][C:10](=[O:13])[CH2:11][CH3:12])[C:23](=[O:24])[C:17]2[C:18](=[CH:19][CH:14]=[CH:15][CH:16]=2)[C:20]1=[O:21]

Participants

4

Reactant 2

HCID 10236NinhydrinHCID 835467N-(3,4-dimethylphenyl)propanamide

Product 1

HCID 71477899HCID 71477899, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(3,4-dimethylphenyl)propion amide (500 mg, 2.82 mmol) and ninhydrin (500 mg, 2.82 mmol) were dissolved in conc. sulfuric acid (10 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 silica gel column chromatography (30% ethylacetate in hexane) to afford the title compound (yellow solid, 430 mg, 45%).

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-edc49fad2eff491aa447832d2ea2e590
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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