Diethyl (ethoxymethylene)malonate → Ethyl 6,7-diethoxy-4-hydroxyquinoline-3-carboxylate

HRID 1090130Notes

Reaction equation

HRID 1090130 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH3:13])[NH2:7])[CH3:2].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>>[CH2:12]([O:11][C:10]1[CH:9]=[C:8]2[C:6](=[CH:5][C:4]=1[O:3][CH2:1][CH3:2])[NH:7][CH:24]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]2=[O:16])[CH3:13]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 5209363,4-Diethoxyaniline

Product 1

HCID 12399898Ethyl 6,7-diethoxy-4-hydroxyquinoline-3-carboxylateYield 69%

Procedure

3,4-Diethoxyaniline (3.7 g) and diethyl ethoxymethylenemalonate (5.3 g) were reacted in the same manner as in Experimental Example 1 to obtain 6,7-diethoxy-3-ethoxycarbonyl-4(1H)-quinolone (4.3 g). The compound (3 g) was subjected to hydrolysis and decarboxylation in the same manner as in Experimental Example 2 to obtain 6,7-diethoxy-4(1H)-quinolone (compound 10, 1.9 g).

Sources & evidence

ORD record
ord-5bac4142372f4589b3c7dbb055691d77
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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