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

HRID 3147

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

Conditions

Temperature: 100 °C

Procedure

A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium bicarbonate in 800 ml of acetic anhydride was stirred under heating at 100° C. for 15 hours. After evaporation of the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate.

Workup

customAfter evaporation of the solvent under reduced pressure, water
additionwas added
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-6ea71cac5fe24314936a22d13c05f389
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733917

Linked notes

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