Diethyl (ethoxymethylene)malonate → 6,7-Dimethoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1090128Notes

Reaction equation

HRID 1090128 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>>[CH3:11][O:10][C:9]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[NH:6][CH:22]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]2=[O:14]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 227703,4-Dimethoxyaniline

Product 1

HCID 100391496,7-Dimethoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl esterYield 40.5%

Procedure

3,4-Dimethoxyaniline (3.0 g) and diethyl ethoxymethylenemalonate (5.1 g) were subjected to condensation and ring closure in the same manner as in Experimental Example 1 to give 6,7-dimethoxy-3-ethoxycarbonyl-4(1H)-quinolone (2.2 g).

Sources & evidence

ORD record
ord-bfdb5d2a54a647f4862cd76f4cdd5012
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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