Acetic Acid → 5-Nitroquinoline-8-carboxylic acid

HRID 501541

Reaktionsgleichung

Reaktionsgleichung von HRID 501541
CC1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[OH-].[Na+].[CH3:17][C:18]([OH:20])=[O:19]>OS(O)(=O)=O.O>[N+:12]([C:5]1[CH:4]=[CH:3][C:17]([C:18]([OH:20])=[O:19])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2463008-Methyl-5-nitroquinoline

Produkt 1

HCID 154053315-Nitroquinoline-8-carboxylic acidAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Compound 12A (1.0 g, 5.3 mmol) was dissolved in concentrated H2SO4 (7 mL), cooled to 0° C., and then CrO3 (2.12 g, 21.3 mmol) was added portionwise over 30 min. After the addition, the reaction mixture was warmed to rt and then heated to 80° C. for 1 h. After cooling to rt, the reaction was diluted with water, basified with 15% aqueous NaOH, then reacidified to pH=3 with AcOH, and extracted with EtOAc (4×100 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound (760 mg, 66%) as a yellow solid. LC/MS m/z 219 [M+H]+.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warmed to rt
  3. temperatureheated to 80° C. for 1 h
  4. temperatureAfter cooling to rt
  5. extractionextracted with EtOAc (4×100 mL)
  6. washThe combined EtOAc extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-86751e0cefa9404ba1643119adc71dd1
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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