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

HRID 1290893

Reaction equation

HRID 1290893 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylateYield 147.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0b38fcc32af04d938445b2572f71a4d6
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Linked notes

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