5-methyl-3-phenyl-6-(2-pyridyl)-isoxazolo[4,5-c]pyridin-4(5H)-one → 3-(alpha-iminobenzyl)-4-hydroxy-6-(2-pyridyl)-1-methyl-2(1H)-pyridone

HRID 461801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 461801
[CH3:1][N:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][C:5]2[O:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:3]1=[O:23].[H][H]>[Pd].C(O)C>[NH:15]=[C:16]([C:4]1[C:3](=[O:23])[N:2]([CH3:1])[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][C:5]=1[OH:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 221377335-methyl-3-phenyl-6-(2-pyridyl)-isoxazolo[4,5-c]pyridin-4(5H)-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1357218413-(alpha-iminobenzyl)-4-hydroxy-6-(2-pyridyl)-1-methyl-2(1H)-pyridone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 16.5 g. (0.0545 mole) of 5-methyl-3-phenyl-6-(2-pyridyl)-isoxazolo[4,5-c]pyridin-4(5H)-one, 330 ml. ethanol and 1.65 g. 10% palladium on carbon is hydrogenated at 50 psi and room temperature. The hydrogenation is ceased after one equivalent of hydrogen is absorbed (ca. 2.5 hours). The mixture is treated with methylene chloride and the catalyst is removed by filtration. The solvents are removed in vacuo to a volume of ca. 50 ml. and then ether is added, to precipitate solids which are removed by filtration to give 3-(α-iminobenzyl)-4-hydroxy-6-(2-pyridyl)-1-methyl-2(1H)-pyridone; m.p. 242° to 245° C. In order to obtain the sodium salt of the aforementioned compound, for example, the compound is dissolved in methanol and treated with sodium hydroxide solution to yield after evaporation the sodium salt.

Aufarbeitung

  1. additionA mixture of 16.5 g
  2. customis hydrogenated at 50 psi and room temperature
  3. customis absorbed (ca. 2.5 hours)
  4. additionThe mixture is treated with methylene chloride
  5. customthe catalyst is removed by filtration
  6. customThe solvents are removed in vacuo to a volume of ca. 50 ml
  7. additionand then ether is added
  8. customto precipitate solids which
  9. customare removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-39c8acbb9d4c4ea0b1cafff561ec959d
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04064251

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