Diethyl (ethoxymethylene)malonate → HCID 19914484, compound

HRID 1090134Notes

Reaction equation

HRID 1090134 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([S:10][CH3:11])[CH:4]=1.C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>>[CH2:20]([O:19][C:17]([C:16]1[C:15](=[O:14])[C:8]2[C:6](=[C:5]([S:10][CH3:11])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=2)[NH:7][CH:22]=1)=[O:18])[CH3:21]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 111479664-methoxy-2-(methylthio)aniline

Product 1

HCID 19914484HCID 19914484, compoundYield 81.5%

Procedure

4-Methoxy-2-methylsulfenylaniline (1.5 g) and diethyl ethoxymethylenemalonate (1.9 g) were reacted in the same manner as in Experimental Example 1 to obtain 3-ethoxycarbonyl-6-methoxy-8-methylsulfenyl-4(1H)-quinolone (2.1 g). The compound (1.3 g) was subjected to hydrolysis and decarboxylation in the same manner as in Experimental Example 2 to obtain 6-methoxy-8-methylsulfenyl-4(1H)-quinolone (compound 30, 0.95 g).

Sources & evidence

ORD record
ord-e342e284f22f46e2ac167fc1c2370bba
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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