Triethylamine → 2-(Pivaloylamino)pyridine

HRID 1815983Notes

Reaction equation

HRID 1815983 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[C:15]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridineYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminopyridine (94.12 g, 1 mole) and Et3N (167.3 mL, 1.2 mole) in CH2Cl2 (1 L) was added pivaloyl chloride (135.5 mL, 1.1 mole) dropwise at 0° C. The mixture was allowed to warm to RT as the bath warmed. After 18 hr the mixture was filtered. The filtrate was washed sequentially with H2O (1.5 L) and saturated NaHCO3 (2×1.5 L), then was dried (MgSO4)and concentrated under reduced pressure to give the title compound (183 g, 103%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 8.28 (m, 2H), 8.00 (br s, 1 H), 7.70 (m, 1 H), 7.03 (m, 1 H), 1.31 (s, 9 H); MS (ES) m/e 179 (M+H)+.

Workup

  1. temperaturewarmed
  2. filtrationAfter 18 hr the mixture was filtered
  3. washThe filtrate was washed sequentially with H2O (1.5 L) and saturated NaHCO3 (2×1.5 L)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d51198592ace483bba6706eb0ca88744
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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