3-Cyclopropyl-3-Oxopropionic Acid Methyl Ester → Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate

HRID 23771

Reaktionsgleichung

Reaktionsgleichung von HRID 23771
[CH:1]1([C:4](=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.CS(O)(=O)=O.[NH2:16][C:17]1[CH:31]=[CH:30][CH:29]=[CH:28][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=O>CC(O)C>[CH:1]1([C:4]2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:18]3[C:17](=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:16]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 53446970(2-Aminophenyl)(4-fluorophenyl)methanone methanesulfonate

Produkt 1

HCID 9901664Methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

12 g of methyl 3-cyclopropyl-3-oxopropionate and 25 g of 2-amino-4′-fluorobenzophenone methanesulfonate were added to 146 g of 2-propanol, and 2-propanol was distilled off at 79 to 83° C. After distilling off 119 g of 2-propanol over 6 hours, 1.14 g of methyl 3-cyclopropyl-3-oxopropionate was added and the mixture was heated at 79 to 81° C. for 4 hours. An analysis of the mixture with high performance liquid chromatography (HPLC) showed that the residual amount of 2-amino-4′-fluorobenzophenone as a raw material was 0.9%. 146 g of toluene was added into the reaction solution, and the reaction solution was washed with 80 g of 4% aqueous solution of sodium hydroxide and then 35 g of 2% aqueous solution of sodium hydroxide. The reaction solution was further washed with 25 g of 5% brine solution, and then dried over 5 g of anhydrous magnesium sulfate. Toluene was removed under a reduced pressure, and crystallization was carried out in 180 g of cyclohexane to obtain 22.9 g of methyl 2-cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carboxylate.

Aufarbeitung

  1. distillationwas distilled off at 79 to 83° C
  2. distillationAfter distilling off 119 g of 2-propanol over 6 hours
  3. addition1.14 g of methyl 3-cyclopropyl-3-oxopropionate was added
  4. addition146 g of toluene was added into the reaction solution
  5. washthe reaction solution was washed with 80 g of 4% aqueous solution of sodium hydroxide
  6. washThe reaction solution was further washed with 25 g of 5% brine solution
  7. dry with materialdried over 5 g of anhydrous magnesium sulfate
  8. customToluene was removed under a reduced pressure, and crystallization

Quellen und Nachweise

ORD-Eintrag
ord-f712a1cdd446458499e3e4380cc15777
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852862B2

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