Diethyl Ether → HCID 54737589, compound
Reaction equation
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[NH:11][CH2:12][CH3:13].C([CH:17]([C:21](Cl)=[O:22])[C:18](Cl)=[O:19])C.[CH2:24]([O:26]CC)[CH3:25]>>[CH2:24]([O:26][C:21]([C:17]1[C:18](=[O:19])[N:11]([CH2:12][CH3:13])[C:5]2[C:4]([C:3]=1[OH:14])=[CH:9][CH:8]=[C:7]([CH3:10])[N:6]=2)=[O:22])[CH3:25]Participants
4
Procedure
To a solution of 3.98 g. (0.02 mole) of 2-ethylamino-6-methylnicotinic acid methyl ester in 50 ml. of anhydrous diethyl ether was added 1.5 g. (0.01 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was added to a solution of 0.23 g. of sodium in 50 ml. of absolute ethanol and was warmed for 5 minutes. The mixture was cooled and the insoluble material was collected and was dissolved in water. Acidification of the water solution with glacial acetic acid afforded a precipitate which was collected, air dried and was recrystallized from heptane to give 1.2 g. of product, m.p. 147°-151° C.
Workup
- filtrationThe mixture was filtered
- customthe filtrate was evaporated in a rotary evaporator
- additionThe residue was added to a solution of 0.23 g
- temperatureof absolute ethanol and was warmed for 5 minutes
- temperatureThe mixture was cooled
- customthe insoluble material was collected
- dissolutionwas dissolved in water
- customAcidification of the water solution with glacial acetic acid afforded a precipitate which
- customwas collected
- customair dried
- customwas recrystallized from heptane
- customto give 1.2 g
Sources & evidence
- ORD record
- ord-a5e82eacdee54f9788de7a82aaca2d8c
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215123
Reaction notes
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