2-Amino-3-benzyloxypyridine → 8-Benzyloxy-3-allyl-2-methylimidazo[1,2-a]pyridine

HRID 4299

Reaktionsgleichung

Reaktionsgleichung von HRID 4299
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH:17]([CH2:21][CH:22]=[CH2:23])[C:18](=O)[CH3:19]>C(O)C>[CH2:9]([O:8][C:7]1[C:2]2[N:3]([C:17]([CH2:21][CH:22]=[CH2:23])=[C:18]([CH3:19])[N:1]=2)[CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 903342-Amino-3-benzyloxypyridineHCID 201523333-Chloro-5-hexen-2-one

Produkt 1

HCID 138258958-Benzyloxy-3-allyl-2-methylimidazo[1,2-a]pyridineAusbeute 7,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-3-benzyloxypyridine (3 g) and 3-chloro-5-hexen-2-one (2.981 g) in ethanol (15 ml) was stirred and refluxed for 45 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using methylene chloride and then chloroform as eluents. The eluate with chloroform was evaporated in vacuo and the residual solid was recrystallized from diisopropyl ether to give 8-benzyloxy-3-allyl-2-methylimidazo[1,2-a]pyridine (0.31 g).

Aufarbeitung

  1. temperaturerefluxed for 45 hours
  2. customevaporated in vacuo
  3. additionTo the residue was added an aqueous solution of sodium bicarbonate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe oily residue was purified by column chromatography on silica gel (50 g)
  9. customThe eluate with chloroform was evaporated in vacuo
  10. customthe residual solid was recrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-185e83baf0c3403dab14950827063d22
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725601

Verknüpfte Notizen

Wird geladen…