Diethyl (ethoxymethylene)malonate → GNF-PF-4421

HRID 1090140Notes

Reaction equation

HRID 1090140 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>>[CH2:18]([O:17][C:15]([C:14]1[C:13](=[O:12])[C:8]2[C:6](=[CH:5][CH:4]=[C:3]([CH2:1][CH3:2])[CH:9]=2)[NH:7][CH:20]=1)=[O:16])[CH3:19]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 115044-Ethylaniline

Product 1

HCID 684193GNF-PF-4421Yield 35.6%

Procedure

p-Ethylaniline (5.0 g) and diethyl ethoxymethylenemalonate (10.7 g) were reacted in the same manner as in Experimental Example 1 to give 3-ethoxycarbonyl-6-ethyl-4(1H)-quinolone (3.6 g). The compound (2.8 g) was N-ethylated with potassium carbonate (2.3 g) and ethyl iodide (2.1 g) in the same manner as in Experimental Example 9 to give 1,6-diethyl-3-ethoxycarbonyl-4(1H)-quinolone (compound 85, 1.55 g).

Sources & evidence

ORD record
ord-50773bebf6d64dca970ccd1599b79217
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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