Diethyl Ether → Ethyl 4-hydroxy-7-methyl-2-oxo-1-propyl-1,2-dihydro-1,8-naphthyridine-3-carboxylate
Reaction equation
CO[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[NH:11][CH2:12][CH2:13][CH3:14].C([CH:18]([C:22](Cl)=[O:23])[C:19](Cl)=[O:20])C.[CH2:25]([O:27]CC)[CH3:26]>>[CH2:25]([O:27][C:22]([C:18]1[C:19](=[O:20])[N:11]([CH2:12][CH2:13][CH3:14])[C:5]2[C:4]([C:3]=1[OH:15])=[CH:9][CH:8]=[C:7]([CH3:10])[N:6]=2)=[O:23])[CH3:26]Participants
Procedure
To a solution of 30.7 g. (0.015 mole) of methyl-2-propylaminonicotinic acid methyl ester in 250 ml. of anhydrous diethyl ether was added 11.25 g. (0.0075 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 2 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was dissolved in 20 ml. of ethanol and this solution was added to a solution of 3.4 g. (0.015 g. atom) of sodium in 200 ml. of ethanol. After stirring at room temperature for 5 minutes, the mixture was diluted with water and was acidified with concentrated hydrochloric acid. The precipitate which formed was collected, air dried and was recrystallized from heptane to afford 3.4 g. of the title compound, m.p. 128°-30° C.
Workup
- filtrationThe mixture was filtered
- customthe filtrate was evaporated in a rotary evaporator
- dissolutionThe residue was dissolved in 20 ml
- additionof ethanol and this solution was added to a solution of 3.4 g
- stirringAfter stirring at room temperature for 5 minutes
- additionthe mixture was diluted with water
- customThe precipitate which formed
- customwas collected
- customair dried
- customwas recrystallized from heptane
- customto afford 3.4 g
Sources & evidence
- ORD record
- ord-e0108d042df44971b621b7e1ae62ffbb
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215123
Reaction notes
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