gamma-Octalactone → 4-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 2118739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118739
[C:1]1([NH:7][C:8]2[N:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:27][C:25](=[O:26])[CH2:24][CH2:23]1.CC(C)([O-])C.[K+]>[OH-].[Na+]>[OH:12][C:10]1[C:9]2[C:8](=[N:17][CH:16]=[CH:15][CH:14]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:25](=[O:26])[C:24]=1[CH2:23][CH:22]([OH:27])[CH2:21][CH2:20][CH2:19][CH3:18]

Komponenten

5

Edukt 3

HCID 7704gamma-OctalactoneHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 547178204-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of methyl 2-phenylaminonicotinate (5 g.), gamma-octanoic lactone (10 g.) and potassium t-butoxide (7.5 g.) was stirred in a nitrogen atmosphere and heated to 95° C. where it was held for 6 hrs. After cooling, the mixture was poured into 5% NaOH (200 ml.) and stirred overnight. Acidification to pH 4.6 yielded an oil, which was extracted with ether, washed with water, dried (Na2SO4), filtered, and evaporated to a small volume. Hexane was added until turbidity was noticed, and the mixture was allowed to stand for about 5 hrs. The solid was filtered off and recrystallized from CH2Cl2 /isopropanol/isopropyl ether to produce the desired product, m.p. 184°-186° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. stirringstirred overnight
  3. customAcidification to pH 4.6 yielded an oil, which
  4. extractionwas extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to a small volume
  9. additionHexane was added until turbidity
  10. waitto stand for about 5 hrs
  11. filtrationThe solid was filtered off
  12. customrecrystallized from CH2Cl2 /isopropanol/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2cd1a0e8b0a4491ca60120a9bc71dd5b
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04680298

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