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

HRID 1442766Notes

Reaction equation

HRID 1442766 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, 9 H), 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-405eb68871b4408da638233545195055
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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