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

HRID 2420878Notes

Reaction equation

HRID 2420878 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.CCN(CC)CC.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 15332-Amino-4-methylpyridineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 35314852,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylpyridin-2-amine (25.0 g, 0.230 mol) and Et3N (35.0 g, 0.350 mmol) in CH2Cl2 (200 ml) was added pivaloyl chloride (33.1 g, 0.270 mol) drop-wise. The mixture was stirred for 4 h under N2 atmosphere. The reaction mixture was quenched with water and was extracted with ethyl acetate (200 mL×3). The combined organic extracts were dried over anhydrous Na2SO4, evaporated under vacuum and purified by chromatography on silica gel (20% ethyl acetate in petroleum ether) to afford N-(4-methylpyridin-2-yl)pivalamide (36.2 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 8.08-8.09 (m, 2H), 8.00 (br s, 1H), 6.83 (dd, J=4.8, 0.6 Hz, 1H), 2.33 (s, 3H), 1.30 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionwas extracted with ethyl acetate (200 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. custompurified by chromatography on silica gel (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cdf9c8ead2d64ddc931e6b5bbdc22212
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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