Ninhydrin → HCID 90097581, compound

HRID 527172Notes

Reaction equation

HRID 527172 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]([OH:13])(O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>OS(O)(=O)=O>[OH:13][C:9]1([C:19]2[CH:20]=[C:21]([O:22][CH3:23])[C:16]([O:15][CH3:14])=[CH:17][C:18]=2[NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[C:10](=[O:11])[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7]1=[O:8]

Participants

4

Reactant 2

HCID 10236NinhydrinHCID 1040180HCID 1040180, compound

Product 1

HCID 90097581HCID 90097581, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Ninhydrin (1.00 g, 5.6 mmol) was dissolved in conc.H2SO4 (10 ml). This solution was added with N-(3,4-dimethoxyphenyl)isobutyramide (1.25 g, 5.62 mmol) at 0° C. and stirred for 30 min under room temperature. Ice water was added with the reaction mixture, and then washed with ice water and ethylacetate. After drying and filtrating, the ethylacetate layer was purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (1.37 g, 63%).

Workup

  1. washwashed with ice water and ethylacetate
  2. customAfter drying
  3. filtrationfiltrating
  4. customthe ethylacetate layer was purified

Sources & evidence

ORD record
ord-40cdafea044945a094bce2521e3d92e0
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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