Hydrogen Peroxide → 2-(2,2-Dimethoxyethyl)nicotinamide

HRID 883904Notes

Reaction equation

HRID 883904 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].C(=O)([O-])[O-:16].[Na+].[Na+].OO>CO>[CH3:14][O:13][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]([NH2:8])=[O:16]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 134111172-(2,2-Dimethoxyethyl)nicotinonitrile

Product 1

HCID 134111212-(2,2-Dimethoxyethyl)nicotinamideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 36b (1.46 g, 7.6 mmol) was dissolved in methanol (20 mL) to which was added at room temperature sodium carbonate as a 3N solution (35 mL) followed by hydrogen peroxide as a 15% solution (35 mL). The reaction was allowed to stir for 4.5 hours then partitioned by the addition of ethyl acetate and solid sodium chloride. The aqueous phase was extracted several times with ethyl acetate and the combined organics stirred with solid sodium bisulfite followed by drying over MgSO4, filtered and concentration under vacuum to give the title compound (1.36 g, 85%) sufficiently pure for use as isolated.

Workup

  1. customthen partitioned by the addition of ethyl acetate and solid sodium chloride
  2. extractionThe aqueous phase was extracted several times with ethyl acetate
  3. stirringthe combined organics stirred with solid sodium bisulfite
  4. dry with materialby drying over MgSO4
  5. filtrationfiltered
  6. concentrationconcentration under vacuum

Sources & evidence

ORD record
ord-e975a9d69d854e33b74295d592ce48fc
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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