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

HRID 869874Notes

Reaction equation

HRID 869874 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-6d95b3aa93054b24a4baa1adfab7919b
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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