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

HRID 1772014Notes

Reaction equation

HRID 1772014 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>CC(C)=O>[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 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(2,2-dimethoxyethyl)nicotinonitrile (7 g, 36.42 mmol), aqueous Na2CO3 (3 N, 145 mL), H2O2 (15%, 145 mL) in acetone (73 mL) was stirred at room temperature for 14 h. After removal of acetone, the residue was diluted with water and extracted with DCM (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 1:1 and with EtOAc) to yield 2-(2,2-dimethoxyethyl)nicotinamide as a solid (6 g, yield 78%). ESI MS: m/z 211 [M+H]+, 233 [M+Na]+.

Workup

  1. customAfter removal of acetone
  2. additionthe residue was diluted with water
  3. extractionextracted with DCM (3×100 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. customThe crude product was purified by silica gel column chromatography (
  10. washeluting with PE/EtOAc v/v 1:1 and with EtOAc)

Sources & evidence

ORD record
ord-11232ef56b884c668d0641f746b3a674
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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