Ethanol → Ninhydrin

HRID 2051425Notes

Reaction equation

NC1C(O)=C2C([CH:6]3[CH:11]([C:12]2=[O:16])[CH2:10][CH2:9][CH2:8][CH2:7]3)=C(C)C=1.C([O:21][C:22](=[O:24])[CH3:23])(=O)C.C([OH:27])C>>[CH:7]1[CH:6]=[C:11]2[C:12]([C:22]([OH:21])([OH:24])[C:23](=[O:27])[C:10]2=[CH:9][CH:8]=1)=[O:16]

Participants

Reactant 3

HCID 702Ethanol

HCID 7918Acetic Anhydride

HCID 151572247-Amino-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 10236Ninhydrin

Procedure

1.0 Gram of 7-amino-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone was dissolved in 30 ml of ethanol and 0.5 ml of acetic anhydride was added. The solution was stirred at room temperature for 1 hour. After disappearance of the color formed by ninhydrin was confirmed on a thin-layer chromatography, the reaction mixture was concentrated. To the residue was added diisopropyl ether and the resulting precipitate was collected by filtration to obtain 0.8 g of 7-acetylamino-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone (light brown crystal).

Sources & evidence

ORD record: ord-09304b82a88e4761a6631337edd816a4
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05017724

Reaction notes

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