Acetic Acid → Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate

HRID 1290894

Reaction equation

HRID 1290894 reaction equation
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]1=[O:20])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 110410352-((Propan-2-yl)amino)benzaldehyde

Product 1

HCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylateYield 163.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 20.0 g of 2-isopropylaminobenzaldehyde, 29.4 g of diethyl malonate, 10 ml of piperidine, 10 ml of acetic acid and 500 ml of toluene was heated to reflux for 13 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 52 g of ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate as the crude product.

Workup

  1. temperatureto reflux for 13 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-25437f40d43f43cbb58bd11a5bdc9e43
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Linked notes

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