Formic Acid → Flosequinan

HRID 1089772

Reaktionsgleichung

Reaktionsgleichung von HRID 1089772
[C:1](OC(=O)C)(=O)C.C(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[CH2:19][S:20]([CH3:22])=[O:21])=[C:14]([NH:24][CH3:25])[CH:13]=1>O>[F:11][C:12]1[CH:13]=[C:14]2[C:15]([C:18](=[O:23])[C:19]([S:20]([CH3:22])=[O:21])=[CH:25][N:24]2[CH3:1])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 10059700Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-

Produkt 1

HCID 4474062Flosequinan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of acetic anhydride (66.0 ml) and formic acid (45.0 ml) was stirred and heated at 50°-60° under nitrogen for 2 hours and then cooled to ambient temperature. 1-(4-Fluoro-2-methylaminophenyl)-2-methylsulphinylethanone (69.0 g), prepared in a similar manner to that described in Example 1, was added slowly below 30° and the mixture stirred for a further 2 hours. The mixture was cooled in an ice/salt bath to 0° and water (500 ml) added whilst maintaining the temperature below 30°. The mixture was filtered and the filtrate cooled in an ice/salt bath to 0°. Toluene (100 ml) and aqueous sodium hydroxide solution (specific gravity 1.5; 140 ml) were added sequentially, again maintaining the temperature below 30°. The mixture was stirred for 30 minutes at ambient temperature and the product collected by filtration, washed with water (200 ml), toluene (3×50 ml) and hexane (2×50 ml) and then dried at 50° in vacuo to give 7-fluoro-1-methyl-3-methylsulphinyl-4-quinolone, m.p.228.5°-230.5° (53.7 g).

Aufarbeitung

  1. temperatureheated at 50°-60° under nitrogen for 2 hours
  2. additionwas added slowly below 30°
  3. stirringthe mixture stirred for a further 2 hours
  4. temperatureThe mixture was cooled in an ice/salt bath to 0°
  5. temperaturewhilst maintaining the temperature below 30°
  6. filtrationThe mixture was filtered
  7. temperaturethe filtrate cooled in an ice/salt bath to 0°
  8. additionToluene (100 ml) and aqueous sodium hydroxide solution (specific gravity 1.5; 140 ml) were added sequentially
  9. temperatureagain maintaining the temperature below 30°
  10. stirringThe mixture was stirred for 30 minutes at ambient temperature
  11. filtrationthe product collected by filtration
  12. washwashed with water (200 ml), toluene (3×50 ml) and hexane (2×50 ml)
  13. customdried at 50° in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bb0c9187cb1241bfbf02c4bcf2a1127c
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079264

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