Hydrogen Peroxide → 1-(2,6-Dimethyl-4-nitrophenyl)-3-(2-hydroxyethyl)pyridin-2(1H)-one

HRID 452243Notes

Reaction equation

HRID 452243 reaction equation
C12BC(CCC1)CCC2.[CH3:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13]([CH3:20])[C:12]=1[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[CH2:28])[C:22]1=[O:29].[OH-].[Na+].OO.S(=O)(O)[O-:35].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[CH3:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13]([CH3:20])[C:12]=1[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][OH:35])[C:22]1=[O:29]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 23665763Sodium BisulfiteHCID 59410169HCID 59410169, compound

Product 1

HCID 545754381-(2,6-Dimethyl-4-nitrophenyl)-3-(2-hydroxyethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

With ice-cooling, a solution of 902 mg (7.40 mmol) of 9-borabicyclo[3.3.1]nonane in 14.8 ml tetrahydrofuran is added to 800 mg (2.96 mmol) of the compound from Example 52A. The mixture is stirred at room temperature for 3 h and then cooled to 0° C., and an aqueous solution of 591 mg (14.8 mmol) of sodium hydroxide is added over a period of 15 min. 2.60 ml of a 30% strength hydrogen peroxide solution are added such that the temperature does not exceed 30° C. After the addition has ended, the mixture is stirred at 0° C. for 30 min. With ice-cooling, a solution of 8.73 g (32.6 mol) of sodium bisulphite in 12 ml of water is added to the reaction mixture. The mixture is diluted with 50 ml of ethyl acetate, the organic phase is removed and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:2). This gives 765 mg (89% of theory) of the desired product.

Workup

  1. temperatureWith ice-cooling
  2. temperaturecooled to 0° C.
  3. customdoes not exceed 30° C
  4. additionAfter the addition
  5. stirringthe mixture is stirred at 0° C. for 30 min
  6. temperatureWith ice-cooling
  7. customthe organic phase is removed
  8. extractionthe aqueous phase is extracted twice with ethyl acetate
  9. washThe combined organic phases are washed with saturated sodium chloride solution
  10. dry with materialdried over sodium sulphate
  11. customevaporated to dryness under reduced pressure
  12. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-d08e7b6e65e54e89942f6ca94212b94e
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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