Benzil → 2,3-Diphenylpyrido[2,3-b]pyrazine

HRID 406242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406242
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:18]=1[NH2:24]>CO.C(O)(=O)C>[C:1]1([C:7]2[N:23]=[C:19]3[CH:20]=[CH:21][CH:22]=[N:17][C:18]3=[N:24][C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 8651BenzilHCID 99562,3-Diaminopyridine

Produkt 1

HCID 8175662,3-Diphenylpyrido[2,3-b]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of benzil (45.7 g, 217 mmol) and pyridine-2,3-diamine (23.7 g, 217 mmol) in methanol (514 ml) and acetic acid (57 ml) was heated at 160° C. for 10 mins using microwave radiation. The reaction mixture was concentrated in vacuo. To the crude residue in methanol (510 ml) was added activated charcoal (25 g) and the suspension was stirred at 60° C. for 1 h. The suspension was filtered hot, cooled and then was stirred in an ice bath. The solid was filtered, washed with cold methanol (50 ml) and dried in vacuo at 40° C. overnight to afford the title compound as pale brown crystals.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the crude residue in methanol (510 ml) was added activated charcoal (25 g)
  3. filtrationThe suspension was filtered hot
  4. temperaturecooled
  5. stirringwas stirred in an ice bath
  6. filtrationThe solid was filtered
  7. washwashed with cold methanol (50 ml)
  8. customdried in vacuo at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-0f9e531578db41f681e0911754de6e29
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754085B2

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