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

HRID 23772

Reaktionsgleichung

Reaktionsgleichung von HRID 23772
[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 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

694.1 kg of methyl 3-cyclopropyl-3-oxopropionate and 1447.8 kg of 2-amino-4′-fluorobenzophenone methanesulfonate were added to 8455 kg of 2-propanol, and 2-propanol was distilled off at 79 to 87° C. After distilling off 7553 kg of 2-propanol, 66.1 kg 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 HPLC showed that the residual amount of 2-amino-4′-fluorobenzophenone as a raw material was 0.5%. 8455 kg of toluene was added into the reaction solution, and the reaction solution was washed with 4620 kg of 4% aqueous solution of sodium hydroxide, then 2010 kg of 2% aqueous solution of sodium hydroxide, and finally 1585 kg of 5% brine solution. The reaction solution was dried over 158 kg of anhydrous magnesium sulfate to obtain 10220 kg of a toluene solution containing 1350 kg of methyl 2-cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carboxylate (converted yield: 90.4%). A part of the solution was concentrated, and the concentrated residue was recrystallized from toluene having the same mass as that of the residue and heptane having five times mass of the residue to obtain methyl 2-cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carboxylate of HPLC purity 99.7%. The substance has the same properties as the substance of Example 1.

Aufarbeitung

  1. distillationwas distilled off at 79 to 87° C
  2. distillationAfter distilling off 7553 kg of 2-propanol, 66.1 kg of methyl 3-cyclopropyl-3-oxopropionate
  3. additionwas added
  4. addition8455 kg of toluene was added into the reaction solution
  5. washthe reaction solution was washed with 4620 kg of 4% aqueous solution of sodium hydroxide
  6. dry with materialThe reaction solution was dried over 158 kg of anhydrous magnesium sulfate
  7. customto obtain 10220 kg of a toluene solution

Quellen und Nachweise

ORD-Eintrag
ord-8ab886e98cda4b66ad7ec1443a3a68a0
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852862B2

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