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

HRID 132217

Reaktionsgleichung

Reaktionsgleichung von HRID 132217
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-20ae7364aea64bc39f849fc707d69485
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384930B2

Verknüpfte Notizen

Wird geladen…