Methanol → 2,6-Diethyl-1,4-dihydro-4-oxopyridine-3-carboxamide

HRID 1614769

Reaktionsgleichung

Reaktionsgleichung von HRID 1614769
[NH2:1][Al](C)C.[CH2:5]([C:7]1[NH:8][C:9]([CH2:18][CH3:19])=[CH:10][C:11](=[O:17])[C:12]=1[C:13](OC)=[O:14])[CH3:6].CO>ClCCl>[CH2:5]([C:7]1[NH:8][C:9]([CH2:18][CH3:19])=[CH:10][C:11](=[O:17])[C:12]=1[C:13]([NH2:1])=[O:14])[CH3:6]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 149504762,6-diethyl-4-hydroxy-3-Pyridinecarboxylic acid methyl esterHCID 16689643Aminodimethyl aluminium

Produkt 1

HCID 151713162,6-Diethyl-1,4-dihydro-4-oxopyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1.3M solution of aminodimethyl aluminium in dichloromethane (obtained as described in Tetrahedron Letters, 1979, 4907) (7.8 ml) was added to a solution of methyl 2,6-diethyl-1,4-dihydro-4-oxopyridine-3-carboxylate (1.05 g in dichloromethane (50 ml) and the solution was left to stand for 20 hours. Methanol (5 ml) was added and the mixture was stirred for 1 hour. The precipitated solid was removed by filtration through a bed of diatomaceous earth. The filtrate was concentrated and the residue purified by flash chromatography, eluting with methanol/dichloromethane (1:9 v/v), to give 2,6-diethyl-1,4-dihydro-4-oxopyridine-3-carboxamide (0.5 g), m.p. 254° C.; NMR (d6 -DMSO): 1.15-1.25(m,6H), 2.5(q,2H), 3.0(q,2H), 6.1(s,1H), 7.0(br s, 1H), 9.6(br s, 1H), 11.3(br s, 1H).

Aufarbeitung

  1. waitthe solution was left
  2. customThe precipitated solid was removed by filtration through a bed of diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by flash chromatography
  5. washeluting with methanol/dichloromethane (1:9 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-a853cc470ee044a283dbf346454c13e9
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05198439

Verknüpfte Notizen

Wird geladen…