Sodium Hydroxide → 7-ethoxy-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

HRID 542816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542816
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[OH-].[Na+].[O-:22][CH2:23][CH3:24].[Na+]>>[CH2:23]([O:22][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1)[CH3:24]

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 2723922Sodium ethoxideHCID 134744537-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

Produkt 1

HCID 134744257-ethoxy-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

Versuchsvorschrift

A mixture of 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone (5.0 g), aqueous sodium hydroxide (5N, 80 ml) and industrial methylated spirit (10 ml) was boiled under reflux for 160 hours. Reaction was incomplete. The hot reaction mixture was filtered and the residue extracted with hot dimethylformamide (40 ml). The extract was evaporated to give a crude product. A mixture of this crude product and ethanolic sodium ethoxide (0.13 g sodium in 110 ml absolute ethanol) was boiled under reflux for 50 hours. The hot reaction mixture was filtered and the filtrate cooled in ice. The precipitate was collected and purified by flash chromatography on Kieselgel 60 using dichloromethane:industrial methylated spirit 9:1 as the eluent. The purified product was recrystallised from industrial methylated spirit to give the novel compound 7-ethoxy-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone, m.p. 214°-217°.

Aufarbeitung

  1. temperatureunder reflux for 160 hours
  2. customReaction
  3. filtrationThe hot reaction mixture was filtered
  4. extractionthe residue extracted with hot dimethylformamide (40 ml)
  5. customThe extract was evaporated
  6. customto give a crude product
  7. temperatureunder reflux for 50 hours
  8. filtrationThe hot reaction mixture was filtered
  9. temperaturethe filtrate cooled in ice
  10. customThe precipitate was collected
  11. custompurified by flash chromatography on Kieselgel 60 using dichloromethane:industrial methylated spirit 9:1 as the eluent
  12. customThe purified product was recrystallised from industrial methylated spirit

Quellen und Nachweise

ORD-Eintrag
ord-310eedd53c0c44f19750afe56c1846c5
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659718

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