Triethylamine → N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

HRID 132352

Reaction equation

HRID 132352 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:14]([CH:15]=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>ClCCl>[CH:15]([C:14]1[C:9]([NH:8][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethlyamine (7.6 mL, 54 mmol), was added to a solution of 2-aminopyridine-3-carboxaldehyde (4.45 g, 36 mmol) in dichloromethane (70 mL). Mixture was cooled to 0° C. A solution of pivaloyl chloride (5.3 mL, 43 mmol) in dichloromethane (30 mL) was added to the mixture. Reaction was warmed to room temperature. Mixture stirred at room temperature for 63 hours. Mixture was washed successively with water (2×50 mL) and brine (30 mL). Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as off-white solid in 90% yield. (M+H)+=207.1.

Workup

  1. customReaction
  2. temperaturewas warmed to room temperature
  3. washMixture was washed successively with water (2×50 mL) and brine (30 mL)
  4. dry with materialOrganic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c58341a15d048099266fe6211fcbb02
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Linked notes

Loading…