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

HRID 2176882Notes

Reaction equation

HRID 2176882 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-900f435d1ed544e8bb7bcccb90c0fc46
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

Loading…