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

HRID 1898941

Reaction equation

HRID 1898941 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].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[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

5

Reactant 3

HCID 7761Diethyl MalonateHCID 516892Sodium BicarbonateHCID 110410352-((Propan-2-yl)amino)benzaldehyde

Product 1

HCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylateYield 61.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium hydrogen carbonate in 80 ml of acetic anhydride was stirred at 100° C. for 15 hours. After the solvent was removed by distillation in vacuo, water was added to the residue. The mixture was then extracted with ethyl acetate. After the organic layer was washed with water and then with saturated sodium bicarbonate aqueous solution, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off in vacuum. The resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate.

Workup

  1. customAfter the solvent was removed by distillation in vacuo, water
  2. additionwas added to the residue
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washAfter the organic layer was washed with water
  5. dry with materialwith saturated sodium bicarbonate aqueous solution, the organic layer was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off in vacuum
  7. customThe resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6cbc130521414ee79d8e151e061a4437
Source dataset
uspto-grants-1996_11
Patent number
US05571820

Linked notes

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