Diethyl (ethoxymethylene)malonate → HCID 19914490, compound

HRID 1090139Notes

Reaction equation

HRID 1090139 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=1[NH2:6])[CH3:2].C([O:15][CH:16]=[C:17]([C:23](OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>>[CH2:1]([O:3][C:4]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:5]=1[NH:6][CH:23]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]2=[O:15])[CH3:2]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 12787082HCID 12787082, compound

Product 1

HCID 19914490HCID 19914490, compoundYield 75.7%

Procedure

2-Ethoxy-4-methoxyaniline (2.2 g) and diethyl ethoxymethylenemalonate (2.9 g) were reacted in the same manner as in Experimental Example 1 to give 8-ethoxy-3-ethoxycarbonyl-6-methoxy-4(1H)-quinolone (2.9 g). The compound (1.5 g) was N-ethylated with potassium carbonate (2.1 g) and ethyl iodide (4.0 g) in the same manner as in Experimental Example 9 to give 8-ethoxy-3-ethoxycarbonyl-1-ethyl-6-methoxy-4(1H)-quinolone (compound 78, 1.3 g).

Sources & evidence

ORD record
ord-a4ae1d2e035548b195486ef8dd215875
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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