Nitric Acid → HCID 21877762, Verbindung

HRID 1922460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922460
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O.O>[F:13][C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Komponenten

5

Edukt 2

HCID 944Nitric AcidHCID 42560293-chloro-N-(2-fluorophenyl)propanamide

Produkt 1

HCID 21877762HCID 21877762, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (see Example 41 for details) (2 g, 12.11 mmol) in sulfuric acid (12 ml), cooled to −5° C. was added nitric acid, 90% (0.565 ml, 12.11 mmol) as a 1:1 solution in water. The reaction mixture was stirred at −5° C. for 20 min, then quenched via addition of ice, precipitating the product which was collected by filtration. The pale solid was then dissolved in dichloromethane, dried, filtered and concentrated, and then chromatographed on silica gel using 0-10% ethyl acetate in dichloromethane as eluent to give the desired 8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (2.33 g, 11.09 mmol, 92% yield). 1H NMR (DMSO-d6) δ 10.73 (brs, 1H), 8.03 (m, 1H), 8.02 (m, 1H), 3.08 (t, J=7.5 Hz, 2H), 2.57 (t, J=7.5 Hz, 1H).

Aufarbeitung

  1. customquenched via addition of ice
  2. customprecipitating the product which
  3. filtrationwas collected by filtration
  4. dissolutionThe pale solid was then dissolved in dichloromethane
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel using 0-10% ethyl acetate in dichloromethane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ffa6994d787a4ccbbece8dbac04ee105
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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