Potassium Permanganate → (8R,9R)-10-acetyl-8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 2249708Notes

Reaction equation

HRID 2249708 reaction equation
C([O:4][C:5]1[C:14]2[CH:13]=[CH:12][N:11]3[C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=[C:10]3[C:9]=2[N:8]([C:20](=[O:22])[CH3:21])[C@H:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1)(=O)C.[Mn]([O-])(=O)(=O)=[O:30].[K+].S([O-])(O)=O.[Na+]>CC(C)=O.O>[C:20]([N:8]1[C:9]2[C:10]3=[N:17][C:16]([CH3:18])=[C:15]([CH3:19])[N:11]3[CH:12]=[CH:13][C:14]=2[C:5](=[O:4])[C@H:6]([OH:30])[C@H:7]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 69289872(9S)-7-acetoxy-10-acetyl-2,3-dimethyl-9-phenyl-9,10-dihydroimidazo[1,2h][1,7]-naphthyridine

Product 1

HCID 69290336(8R,9R)-10-acetyl-8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-oneYield 16%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2.0 g (5.4 mmol) of (9S)-7-acetoxy-10-acetyl-2,3-dimethyl-9-phenyl-9,10-dihydroimidazo[1,2h][1,7]-naphthyridine are dissolved in 30 ml of acetone and 6 ml of water. 1.0 g (6.4 mmol) of potassium permanganate is then introduced in portions at 0° C. After 30 min, the brown suspension is admixed with 1 ml of saturated sodium hydrogensulphite solution, filtered through Celite and washed with methanol and dichloromethane. The filtrate is concentrated and the residue crystallized using ethanol. 0.3 g (16%) of the title compound is isolated as a yellow solid (m.p. 192° C.).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with methanol and dichloromethane
  3. concentrationThe filtrate is concentrated
  4. customthe residue crystallized

Sources & evidence

ORD record
ord-db895a426ff34eccbb7cf1fa90d022c5
Source dataset
uspto-grants-2008_01
Patent number
US07314935B2

Reaction notes

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