Ethanol → HCID 57917364, Verbindung

HRID 1942057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942057
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.O[CH2:13][CH:14]([CH2:16]O)O.[CH3:18][CH2:19][OH:20].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH2:18]([O:7][C:6]([C:5]1[C:4]([F:11])=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:16][CH:14]=[CH:13]2)=[O:8])[CH3:19].[CH2:19]([O:20][C:6]([C:5]1[CH:9]=[C:10]2[C:2](=[CH:3][C:4]=1[F:11])[N:1]=[CH:16][CH:14]=[CH:13]2)=[O:8])[CH3:18]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 753GlycerolHCID 14923Ammonium HydroxideHCID 3026804-Amino-2-fluorobenzoic acid

Produkt 2

HCID 57917364HCID 57917364, VerbindungHCID 57917442Ethyl 5-fluoro-6-quinolinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 4-amino-2-fluoro-benzoic acid (1 g, 6.38 mmol) in sulfuric acid 75% (15 mL) were added glycerol anhydrous (2.108 mL, 28.72 mmol) and sodium 3-nitrosulfonate (2.93 g, 12.8 mmol). The mixture was stirred at 100° C. for 4 h. It was then cooled down to 60° C. and EtOH was added. The mixture was then stirred at 60° C. for 45 h. The solution was poured into ice-water mixture and then basified with saturated aqueous ammonium hydroxide. It was extracted twice with EtOAc. The organic phases were joined and washed with brine, dried over Na2SO4 and concentrated. The residue was purified by MPLC eluting with a DCM/MeOH gradient to afford a yellow oil as a mixture (1:1) of 5-fluoro-quinoline-6-carboxylic acid ethyl ester and 7-fluoro-quinoline-6-carboxylic acid ethyl ester (tR 1.3 min and tR 1.1 min (conditions 6), MH+=220).

Aufarbeitung

  1. temperatureIt was then cooled down to 60° C.
  2. stirringThe mixture was then stirred at 60° C. for 45 h
  3. extractionIt was extracted twice with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC
  8. washeluting with a DCM/MeOH gradient

Quellen und Nachweise

ORD-Eintrag
ord-f0b0b54082d04dc49ccfbc5bd890a6cb
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389526B2

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