3-Nitrobenzaldehyde → 7-(3-Nitrophenyl)-furo[3,4-b]pyridin-5-one

HRID 861949

Reaktionsgleichung

Reaktionsgleichung von HRID 861949
C([C:4]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)(O)=O.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)C=O)([O-:16])=[O:15].CC1C=CC(C(C)C)=CC=1>>[N+:14]([C:17]1[CH:24]=[C:23]([CH:13]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[C:10](=[O:11])[O:12]2)[CH:22]=[CH:19][CH:18]=1)([O-:16])=[O:15]

Komponenten

4

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 7463P-CymeneHCID 2906973-(Methoxycarbonyl)pyridine-2-carboxylic acid

Produkt 1

HCID 700670317-(3-Nitrophenyl)-furo[3,4-b]pyridin-5-oneAusbeute 37,2 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A solution of 2,3-pyridinyldicarboxylic anhydride (20 g, 134 mmoles) in 25 ml of anhydrous methanol was refluxed for 30 minutes. The methanol was removed and the two positional isomers (2-carboxy-3-methoxycarbonylpyridine and 2-methoxycarbonyl-3-carboxypyridine) are isolated and separated. The 2-carboxy-3-methoxycarbonyl pyridine was added to a solution of 3-nitrobenzaldehyde (101.35 g, 670 mmoles) in p-cymene (105 ml, 670 mmoles) and heated at 180° C. for 13.5 hours. The solution was cooled, filtered and the excess 3-nitrobenzaldehyde and p-cymene removed by bulb to bulb distillation using a Kugelrohr apparatus. The residue was triturated with methylene chloride and the solid residue was discarded. The product was isolated from the filtrate yielding 12.7 g of 7-(3-nitrophenyl)-furo[3,4-b]pyridin-5-one (37.2%).

Aufarbeitung

  1. customseparated
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. customthe excess 3-nitrobenzaldehyde and p-cymene removed by bulb to bulb distillation
  5. customThe residue was triturated with methylene chloride
  6. customThe product was isolated from the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-a526cde80d6146ab9414ff7e256ff945
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716954

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