Diethyl Ether → Ethyl 4-hydroxy-1,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate
Reaction equation
[CH3:1][NH:2][C:3]1[N:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].C([CH:16]([C:20](Cl)=[O:21])[C:17](Cl)=[O:18])C.[CH2:23]([O:25]CC)[CH3:24]>>[CH2:23]([O:25][C:20]([C:16]1[C:17](=[O:18])[N:2]([CH3:1])[C:3]2[C:4]([C:5]=1[OH:6])=[CH:9][CH:10]=[C:11]([CH3:13])[N:12]=2)=[O:21])[CH3:24]Participants
4
Procedure
To a solution of 9.0 g. (0.05 mole) of methyl 2-methylamino-6-methylnicotinate in 150 ml. of anhydrous diethyl ether was added 3.75 g. (0.025 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 3 hours. The mixture was filtered and the filtrate was dissolved in 10 ml. of ethanol. This solution was added to a solution of 1.15 g. (0.05 g. atoms) of sodium in 75 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes and was filtered. The filter cake was triturated with 100 ml. of water and this mixture was acidified with glacial acetic acid. The insoluble material was collected, air dried and was recrystallized from ethyl acetate to give 1.5 g. of the title compound, m.p. 143°-5° C.
Workup
- filtrationThe mixture was filtered
- dissolutionthe filtrate was dissolved in 10 ml
- additionThis solution was added to a solution of 1.15 g
- stirringThe mixture was stirred at room temperature for 5 minutes
- filtrationwas filtered
- customThe filter cake was triturated with 100 ml
- customThe insoluble material was collected
- customair dried
- customwas recrystallized from ethyl acetate
- customto give 1.5 g
Sources & evidence
- ORD record
- ord-b4964783806544f3b9b12188f72654c5
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215123
Reaction notes
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