Acetic Acid → 6'-Methyl-2,3'-bipyridine-2'-carboxylic acid

HRID 61093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61093
[CH3:1][C:2]1[N:7]=C(C#N)[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:18][C:19]([OH:21])=[O:20]>CO>[CH3:1][C:2]1[N:7]=[C:18]([C:19]([OH:21])=[O:20])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 593637166'-Methyl-2,3'-bipyridine-2'-carbonitrile

Produkt 1

HCID 593637356'-Methyl-2,3'-bipyridine-2'-carboxylic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

6′-Methyl-[2,3′-bipyridine]-2′-carbonitrile (0.87 g, 4.46 mmol) and NaOH (1.87 g, 46.8 mmol) were dissolved in methanol (3 mL) and stirred at reflux overnight. The reaction was cooled to rt, diluted with more methanol (5 ml), and acidified with AcOH to pH 4-5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a clear oil (0.9 g, 94%).

Aufarbeitung

  1. temperatureat reflux overnight
  2. customThe solvent was removed in vacuo
  3. customto obtain the crude which
  4. customwas purified by silica gel chromatography (0˜100% DCM/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7989130023d04570a080c64d4377acf5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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