Sulfuric Acid → Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

HRID 451222

Reaktionsgleichung

Reaktionsgleichung von HRID 451222
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.[CH:17]1([C:20](=O)[CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:19][CH2:18]1.S(=O)(=O)(O)O>CO>[CH:17]1([C:20]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:4]([C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)[C:3]3[C:2](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:1]=2)[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 98372872-Amino-4'-fluorobenzophenoneHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Produkt 1

HCID 9901664Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To the solution of 2-amino-4′-fluorobenzophenone (100 g) in methanol (500 ml) added Methyl 3-cyclopropyl-3-oxopropanoate (132 g), sulfuric acid (5 ml) and stirred for 15 minutes at 25° C. Heated the reaction mixture to 65° C. for 22 hrs. Distilled off the methanol completely under reduced pressure. Cooled the reaction mixture to 25° C., added water (500 ml) and stirred for 30 minutes. Cooled the reaction mixture to 0° C. and pH adjusted to 6.0 with sodium carbonate solution. Stirred the reaction mixture for 45 minutes at 25° C. Filtered the cake and washed with water. Spin dry the compound for 60 minutes. To this compound added methanol (150 ml) and stirred for 1 hr at 25° C. Filtered the solid and washed with methanol (50 ml). Dried the obtained solid to get the title compound.

Aufarbeitung

  1. temperatureHeated the reaction mixture to 65° C. for 22 hrs
  2. distillationDistilled off the methanol completely under reduced pressure
  3. temperatureCooled the reaction mixture to 25° C.
  4. additionadded water (500 ml)
  5. stirringstirred for 30 minutes
  6. temperatureCooled the reaction mixture to 0° C.
  7. stirringStirred the reaction mixture for 45 minutes at 25° C
  8. filtrationFiltered the cake
  9. washwashed with water
  10. customSpin dry the compound for 60 minutes
  11. additionTo this compound added methanol (150 ml)
  12. stirringstirred for 1 hr at 25° C
  13. filtrationFiltered the solid
  14. washwashed with methanol (50 ml)
  15. customDried the obtained solid

Quellen und Nachweise

ORD-Eintrag
ord-f512dc7c2628429c9c19daab70177297
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487105B2

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