Ninhydrin → HCID 71477900, compound

HRID 527161Notes

Reaction equation

HRID 527161 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[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>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:21]2([OH:24])[C:19](=[O:20])[C:17]3[C:16](=[CH:15][CH:14]=[CH:13][CH:18]=3)[C:22]2=[O:23])=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 10236NinhydrinHCID 4341261N-(3-ethylphenyl)acetamide

Product 1

HCID 71477900HCID 71477900, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(3-ethylphenyl)acetamide (500 mg, 3.06 mmol) and ninhydrin (546 mg, 3.06 mmol) were dissolved in conc. sulfuric acid (10 mL) and stirred at room temperature for 3 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 (90 mg, 9%).

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-947838d5b58c4d089664c49b8f927c3a
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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