Diethyl Malonate → Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate

HRID 1290893

Reaktionsgleichung

Reaktionsgleichung von HRID 1290893
Cl.[CH:2]([NH:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O)([CH3:4])[CH3:3].[C:14](OCC)(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].N1CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH:2]([N:5]1[C:6]2[C:7](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]1=[O:21])([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 189196242-Isopropylaminobenzaldehyde hydrochloride

Produkt 1

HCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylateAusbeute 147,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 133.7 g of 2-isopropylaminobenzaldehyde hydrochloride, 200 g of diethyl malonate, 70 ml of piperidine, 70 ml of acetic acid, 50 g of potassium carbonate and 1.5 liter of toluene was heated to reflux for 10 hours. The reaction solution was washed with water and then with saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off to give 256 g of ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate as the crude product.

Aufarbeitung

  1. temperatureto reflux for 10 hours
  2. washThe reaction solution was washed with water
  3. dry with materialwith saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-0b38fcc32af04d938445b2572f71a4d6
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753673

Verknüpfte Notizen

Wird geladen…