2,2-Dimethyl-N-(5-vinylpyridin-2-yl)-propionamide → N-(5-ethylpyridin-2-yl)pivalamide

HRID 2188893Notes

Reaction equation

HRID 2188893 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:7][CH:8]=1)=[CH2:2]>CCO.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 217020792,2-Dimethyl-N-(5-vinylpyridin-2-yl)-propionamide

Product 1

HCID 59272530N-(5-ethylpyridin-2-yl)pivalamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A catalytic amount of Pd/C was added to a solution of N-(5-vinylpyridin-2-yl)pivalamide (23 g, 0.11 mol) in EtOH (200 mL). The reaction mixture was stirred under hydrogen atmosphere overnight. The catalyst was filtrated off and the solution was concentrated in vacuo to afford N-(5-ethylpyridin-2-yl)pivalamide (22 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 8.15 (d, J=8.4, 1H), 8.09 (d, J=2.4, 1H), 7.96 (br s, 1H), 7.54 (dd, J=8.4 and 2.4, 1H), 2.61 (q, J=7.5, 2H), 1.30 (s, 9H), 1.23 (t, J=7.5, 3H).

Workup

  1. filtrationThe catalyst was filtrated off
  2. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-9ece7b2bc4cc41c280cfd219279972e7
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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