Pyridine → Bia-2-024

HRID 361318

Reaktionsgleichung

Reaktionsgleichung von HRID 361318
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1.Cl.[NH2:21][OH:22].N1C=CC=CC=1>>[OH:22][N:21]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 34312OxcarbazepineHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 85040065Bia-2-024

Versuchsvorschrift

A suspension of 4.0 g (15.86 mmol) of 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide and 3.86 g (55.49 mmol) of hydroxylamine hydrochloride in 100 mL of absolute alcohol was treated with 3.76 g (47.57 mmol) of pyridine. The mixture was heated at reflux for 1 hour and then the ethanol was removed by evaporation under reduced pressure. The residue was partitioned between 150 mL of water and 150 mL of dichloromethane. The organic layer was separated and washed with 50 mL of 1M aqueous HCl, a saturated solution of NaHCO3 and brine, then dried by sodium sulphate. Filtration and evaporation of the solvent under reduced pressure gave an off-white solid which was triturated with hot ethanol to give the desired compound as a white powder of m.p. 230.4° to 231.5° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthe ethanol was removed by evaporation under reduced pressure
  4. customThe residue was partitioned between 150 mL of water and 150 mL of dichloromethane
  5. customThe organic layer was separated
  6. washwashed with 50 mL of 1M aqueous HCl
  7. dry with materiala saturated solution of NaHCO3 and brine, then dried by sodium sulphate
  8. filtrationFiltration and evaporation of the solvent under reduced pressure
  9. customgave an off-white solid which
  10. customwas triturated with hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c416f4cbbac447c38f5cc84c273ef3c8
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866566

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