Water → 2,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamide

HRID 2374157Notes

Reaction equation

HRID 2374157 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12].O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:9][C:10]([CH3:15])([CH3:14])[C:11]([NH:8][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 15332-Amino-4-methylpyridineHCID 62493Pivaloyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 35314852,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-pyridin-2-ylamine (30 g, 0.28 mol) was dissolved in DCM (300 mL) and treated with TEA (41 mL) followed by trimethylacetyl chloride (38 mL) via a dropping funnel over 30 min. The mixture was allowed to stir overnight at RT, then poured into a separatory funnel with water (100 mL) and satd. aq. NaHCO3 (75 mL). The organic layer was extracted, washed with satd. aq. NaHCO3 (75 mL), dried over Na2SO4, and concentrated to give solid 2,2-dimethyl-N-(4-methyl-pyridin-2-yl)-propionamide (42 g, 0.22 mol). 1H NMR (CDCl3) δ 8.09 (m, 2 H), 7.93 (br s, 1 H), 6.83 (m, 1 H), 2.33 (s, 3H), 1.29 (s, 9H).

Workup

  1. extractionThe organic layer was extracted
  2. washwashed with satd
  3. dry with materialaq. NaHCO3 (75 mL), dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4524d4cbc6045baa4d3aa623b955470
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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