Methanol → 6-methoxyquinoline-2-carboxylic Acid

HRID 493422

Reaktionsgleichung

Reaktionsgleichung von HRID 493422
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]#N)[CH:7]=[CH:6]2.[OH-:15].[Na+].C[OH:18]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([OH:18])=[O:15])[CH:7]=[CH:6]2

Komponenten

4

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2304816-Methoxyquinoline-2-carbonitrile

Produkt 1

HCID 111832986-methoxyquinoline-2-carboxylic Acid

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

6-Methoxy-quinoline-2-carbonitrile (9.3 g, 0.050 mol) in 96 ml methanol was treated with 240 ml of 20% NaOH and the mixture was heated to 120° C. in a sealed tube overnight. After cooling to 0° C. a precipitate appeared. The mixture was filtered to get a sodium salt that was suspended in water. HCl 25% was added until pH 3-4 to get the acid as a precipitate that was filtered and dried under vacuum. The mother liquid of the first filtration was acidified with HCl 25% until pH 3-4 until a precipitate appeared. The precipitate was filtered and the solid was washed in water and dried under vacuum to yield 9.6 g (86%) of the title compound as light brown solid. MS (m/e)=204 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to 0° C. a precipitate
  2. filtrationThe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-684a65afc216472785d37d093bb33462
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534891B2

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