Sodium Bicarbonate → 2-(6-Methoxypyridin-3-yl)acetamide

HRID 1896246Notes

Reaction equation

HRID 1896246 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.C(=O)(O)[O-:13].[Na+]>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]([NH2:11])=[O:13])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 45079846(6-Methoxypyridin-3-yl)acetonitrile

Product 1

HCID 673832592-(6-Methoxypyridin-3-yl)acetamideYield 52.2%

Procedure

The compound 2-(6-methoxypyridin-3-yl)acetonitrile (0.60 g, 4.05 mmol) in poly phosphoric acid (6 g) was stirred at 95° C. for 1 h. The reaction mixture was neutralized with saturated sodium bicarbonate solution and the compound was extracted with DCM (3×20 ml). The combined organic layers were washed with brine (15 ml), dried over anhydrous sodium sulfate, filtered and concentrated under vacuo. The crude compound was washed with ether (2×5 ml) to afford 350 mg (52.2%) of 2-(6-methoxypyridin-3-yl)acetamide as white color solid.

Workup

  1. extractionthe compound was extracted with DCM (3×20 ml)
  2. washThe combined organic layers were washed with brine (15 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuo
  6. washThe crude compound was washed with ether (2×5 ml)

Sources & evidence

ORD record
ord-f4e701a5068647e6a80e1e723380faff
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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