Water → 5-[1,1'-Biphenyl]-4-yl-9-fluoro-3-methyl-1H-[1,3]oxazino[4,5-c]quinolin-1-one

HRID 1073254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073254
[NH2:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=[O:13])=[CH:9][C:8]([F:15])=[CH:7][CH:6]=2.O.[C:29](OC(=O)C)(=O)[CH3:30]>S(=O)(=O)(O)O>[C:19]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[CH:21][C:16]([C:3]2[C:2]3[N:1]=[C:29]([CH3:30])[O:13][C:12](=[O:14])[C:11]=3[C:10]3[CH:9]=[C:8]([F:15])[CH:7]=[CH:6][C:5]=3[N:4]=2)=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1314193-Amino-2-(1,1'-biphenyl)-4-yl-6-fluoro-4-quinolinecarboxylic acid

Produkt 1

HCID 150859865-[1,1'-Biphenyl]-4-yl-9-fluoro-3-methyl-1H-[1,3]oxazino[4,5-c]quinolin-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of 4 g of 3-amino-2-[1,1'-biphenyl]-4-yl-6-fluoro-4-quinolinecarboxylic acid in 30 ml of acetic anhydride was added 10 drops of concentrated sulfuric acid. The mixture was heated at 90° C. for 2 hours, then cooled and poured into 200 ml of water. This solution was stirred at 20° C. for 30 minutes, then the resulting solid was collected and washed with water. The residue was dissolved in 150 ml of dichloromethane and washed with 100 ml of saturated aqueous sodium bicarbonate. The organic layer was separated, dried and the volatiles removed in vacuo. The residue was dissolved in a small amount of dichloromethane and passed through a short pad of hydrous magnesium silicate, eluting with dichloromethane:hexane 1:1). The solids which were obtained were recrystallized from dichloromethane/hexane, giving 4.1 g of the desired intermediate as yellow crystals, mp 188°-189° C.

Aufarbeitung

  1. temperaturecooled
  2. customthe resulting solid was collected
  3. washwashed with water
  4. dissolutionThe residue was dissolved in 150 ml of dichloromethane
  5. washwashed with 100 ml of saturated aqueous sodium bicarbonate
  6. customThe organic layer was separated
  7. customdried
  8. customthe volatiles removed in vacuo
  9. dissolutionThe residue was dissolved in a small amount of dichloromethane
  10. washeluting with dichloromethane:hexane 1:1)
  11. customThe solids which were obtained
  12. customwere recrystallized from dichloromethane/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6bee13df2d7d48059d303ad587232381
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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