Sodium Hydroxide → 3-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

HRID 2273260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2273260
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]#[N:13])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2.[OH-:16].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH2:13])=[O:16])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 672545843-Chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile

Produkt 1

HCID 672571323-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile (5.0 g, 22.8 mmol, 1.0 eq) is suspended in a 10% sodium hydroxide aqueous solution (125 mL) and the resulting mixture is heated to reflux for 30 minutes. The reaction mixture is then extracted with ethyl acetate (3×100 mL) and the pH is adjusted to 3-4 by the addition of a 3N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:1 to 4:1, v/v) to afford 3-chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide as an off-white solid (3.44 g, 64% yield).

Aufarbeitung

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 30 minutes
  3. extractionThe reaction mixture is then extracted with ethyl acetate (3×100 mL)
  4. additionthe pH is adjusted to 3-4 by the addition of a 3N hydrochloric acid aqueous solution
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product that
  9. customis purified by column chromatography (silica gel, eluent

Quellen und Nachweise

ORD-Eintrag
ord-761c4c9fd0da4d7089852d126d3a0994
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120822B2

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