Hydrogen Peroxide → 3-(2,2-Dimethoxyethyl)-5-methoxypicolinamide

HRID 930481Notes

Reaction equation

HRID 930481 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[C:6]([C:13]#[N:14])=[N:7][CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1.O.C(=O)([O-])[O-:19].[Na+].[Na+].OO>CC(C)=O>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[C:6]([C:13]([NH2:14])=[O:19])=[N:7][CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 10340Sodium CarbonateHCID 867322873-(2,2-Dimethoxyethyl)-5-methoxypicolinonitrile

Product 1

HCID 867322863-(2,2-Dimethoxyethyl)-5-methoxypicolinamideYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 1 L round-bottomed flask was added 3-(2,2-dimethoxyethyl)-5-methoxypicolinonitrile (8.550 g, 38.5 mmol), water (480 ml), and acetone (120 ml). An aqueous solution of sodium carbonate (3M; 154 ml, 462 mmol) was added followed by hydrogen peroxide (35 wt. % solution in water; 138 ml, 1347 mmol). The tan mixture was stirred vigorously at rt for 2 h. The organic solvent was removed uncle reduced pressure and the aqueous residue was extracted with DCM (3×). The combined organic fractions were dried over sodium sulfate. The filtrate was concentrated under reduced pressure to afford 3-(2,2-dimethoxyethyl)-5-methoxypicolinamide (8.200 g, 34.1 mmol, 89% yield) as an off-white solid that was advanced without further purification. MS m/z=263.2 (M+Na)

Workup

  1. customThe organic solvent was removed uncle reduced pressure
  2. extractionthe aqueous residue was extracted with DCM (3×)
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a60119856e0e48419af5955e32f14713
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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