Hydrogen Peroxide → HCID 87887145, compound

HRID 584841Notes

Reaction equation

HRID 584841 reaction equation
[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-:26].[K+].[K+].OO.C(=O)([O-])O.[Na+]>C(#N)C.CO>[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]2[O:26][C@@H:6]2[C@H:5]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 22341778HCID 22341778, compound

Product 1

HCID 87887145HCID 87887145, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

0.64 g (2 mmol) of rac-10-acetyl-2,3-dimethyl-9-phenyl-9,10-dihydroimidazo[1,2-h][1,7]naphthyridine (racemic) are dissolved in 3 ml of acetonitrile and 1 ml of methanol and treated with 0.18 g (1.2 mmol) of potassium carbonate. 0.2 ml of hydrogen peroxide solution (30% in water) is then slowly added dropwise with ice cooling. The mixture is then allowed to warm to room temperature and is stirred for 16 h. After addition of saturated sodium hydrogencarbonate solution, it is extracted with dichloromethane. The organic phase is dried over magnesium sulfate and evaporated. The residue is purified by chromatography on silica gel (eluent diethyl ether/triethylamine 9:1). After crystallization from diethyl ether, 80 mg (12%) of the title compound are isolated as a colorless solid (m.p. 222° C.).

Workup

  1. extractionis extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated
  4. customThe residue is purified by chromatography on silica gel (eluent diethyl ether/triethylamine 9:1)
  5. customAfter crystallization from diethyl ether, 80 mg (12%) of the title compound

Sources & evidence

ORD record
ord-a6e7d62e7eae4ea1b47ac98b90e22582
Source dataset
uspto-grants-2005_08
Patent number
US06927292B2

Reaction notes

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