Diethyl (ethoxymethylene)malonate → HCID 21829132, compound
Reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[O:11][CH3:12])[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]2[C:7](=[CH:6][C:5]=1[O:11][CH3:12])[NH:8][CH:23]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]2=[O:15])[CH3:2]Participants
3
Procedure
4-Ethoxy-3-methoxyaniline (2.6 g) and diethyl ethoxymethylenemalonate (3.4 g) were reacted in the same manner as in Experimental Example 1 to obtain 6-ethoxy-3-ethoxycarbonyl-7-methoxy-4(1H)-quinolone (2.5 g). The compound (2.3 g) was ethylated with potassium carbonate (3.3 g) and ethyl iodide (6.1 g) in the same manner as in Experimental Example 9 to obtain 6-ethoxy-3-ethoxycarbonyl-1-ethyl-7-methoxy-4(1H)-quinolone (1.8 g). This compound (1.4 g) was hydrolyzed in the same manner as in Experimental Example 9 to obtain a carboxylic acid (1.2 g), which was then decarboxylated in the same manner as in Experimental Example 9 to obtain 6-ethoxy-1-ethyl-7-methoxy-4(1H)-quinolone (compound 49, 210 mg).
Sources & evidence
- ORD record
- ord-4c797cd740794b8eaae4557ec0696953
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05081121
Reaction notes
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