Sodium Bicarbonate → 8-Hydroxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

HRID 61904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61904
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:21])([CH3:20])[C:7]=2[CH:22]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:20])([CH3:21])[C:7]=2[CH:22]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 668342278-Methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

Produkt 1

HCID 668350828-Hydroxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-oneAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
178 °C

Versuchsvorschrift

Mixture of 8-methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b] fluoren-5-one (Compound GT15-4, 25 mg) and pyridine hydrochloric acid salt (492 mg) was stirred and heated at 178° C. overnight. The reaction mixture was cooled, and added with water. The mixture was neutralized with saturated aqueous solution of sodium bicarbonate and extracted with DCM. The organic layer was washed with saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (DCM/MeOH) to obtain the title compound (13 mg, 54%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residues were purified by silica gel column (DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-de8fb03427b34e699e0b38819f1f8c41
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440922B2

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