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Hydrochloric Acid → 1,5-Naphthyridin-3-ylacetic acid

HRID 82231
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 82231
[OH-].[Na+].[N:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH2:13][C:14]([O:16]CC)=[O:15])[CH:4]=1.Cl>O1CCOCC1>[N:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH2:13][C:14]([OH:16])=[O:15])[CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70817520Ethyl 1,5-naphthyridin-3-ylacetate

Produkt 1

HCID 866721091,5-Naphthyridin-3-ylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Sodium hydroxide (10 mL, 2.0 M) was added to ethyl 1,5-naphthyridin-3-ylacetate in 1,4-dioxane (10 mL) and the mixture was heated at 100° C. for 6 hours. The reaction mixture was cooled to room temperature and acidified to pH 4 using aqueous 2M HCl and then evaporated in vacuo. The residue was azeotroped with toluene (2×15 mL) then dissolved in THF (50 mL) and stirred at 40° C. for 30 min. The mixture was filtered, the filtrate was evaporated in vacuo and the residue was triturated with diethyl ether to afford the title compound as an off white solid, 200 mg.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated in vacuo
  3. customThe residue was azeotroped with toluene (2×15 mL)
  4. dissolutionthen dissolved in THF (50 mL)
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated in vacuo
  7. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8cc1783b27924989bf2dfc628360f3b9
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846698B2

Notizen zur Reaktion

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