Diethyl Ether → 6-Methoxy-1,5-naphthyridin-4-ol

HRID 1271677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271677
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:10](OC)(=[O:13])[C:11]#[CH:12].CCOCC>CO.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:5]1[N:6]=[C:7]2[C:2](=[CH:3][CH:4]=1)[NH:1][CH:12]=[CH:11][C:10]2=[O:13]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 13536Methyl propiolateHCID 811216-Methoxy-3-pyridinylamine

Produkt 1

HCID 113788076-Methoxy-1,5-naphthyridin-4-olAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Lösungsmittel2×

Versuchsvorschrift

5-Amino-2-methoxypyridine (55 g, 0.44 mol) in methanol (1000 ml) with methyl propiolate (40 ml, 0.44 mol) was stirred for 48 hours, then evaporated and the product purified by chromatography on silica gel (dichloromethane) followed by recrystallisation from dichloromethane-hexane (44.6 g, 48%). The unsaturated ester (10.5 g, 0.05 mol) in warm Dowtherm A (50 ml) was added over 3 minutes to refluxing Dowtherm A, and after a further 20 minutes at reflux the mixture was cooled and poured into ether. The precipate was filtered to give a white solid (6.26 g, 70%).

Aufarbeitung

  1. customevaporated
  2. customthe product purified by chromatography on silica gel (dichloromethane)
  3. customfollowed by recrystallisation from dichloromethane-hexane (44.6 g, 48%)
  4. temperatureafter a further 20 minutes at reflux the mixture
  5. temperaturewas cooled
  6. filtrationThe precipate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-3a8cfa113d31424082fba6eedaa5d3e3
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205408B2

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