Potassium Permanganate → (8r,9r)-3-Formyl-8-hydroxy-2-methyl-7-oxo-9-phenyl-7,8,9,10tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 1530883Notes

Reaction equation

HRID 1530883 reaction equation
[OH:1][C@H:2]1[C:11](=[O:12])[C:10]2[CH:9]=[CH:8][N:7]3[C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=[C:6]3[C:5]=2[NH:4][C@@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Mn]([O-])(=O)(=O)=[O:25].[K+]>C(Cl)(Cl)Cl>[CH:17]([C:13]1[N:7]2[CH:8]=[CH:9][C:10]3[C:11](=[O:12])[C@H:2]([OH:1])[C@@H:3]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:4][C:5]=3[C:6]2=[N:15][C:14]=1[CH3:16])=[O:25]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 59943673(8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 20640288(8r,9r)-3-Formyl-8-hydroxy-2-methyl-7-oxo-9-phenyl-7,8,9,10tetrahydroimidazo[1,2-h][1,7]naphthyridineYield 6.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(8R,9R)-8-hydroxy-2,3-dimethyl-7-oxo-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine (1 g) is dissolved in 20 ml of dried chloroform, and 5 g of potassium permanganate was added. After stirring the reaction mixture at room temperature for 40 days, the solids are filtered off. The filtrate is chromatographed twice on silica gel (eluents: dichloromethane/methanol 13/1) to give 0.07 g of the title compound as a semisolid.

Workup

  1. filtrationthe solids are filtered off
  2. customThe filtrate is chromatographed twice on silica gel (eluents: dichloromethane/methanol 13/1)

Sources & evidence

ORD record
ord-e6be2b58566842f7acc90319442fdd71
Source dataset
uspto-grants-2001_03
Patent number
US06197783B1

Reaction notes

Loading…