Diethyl Ether → Ethyl 1-allyl-4-hydroxy-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

To a solution of 2.88 g. (0.015 mole) of 2-allylamino-6-methylnicotinic acid, methyl ester in 50 ml. of anhydrous diethyl ether was added 1.12 g. (0.0075 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 4 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was dissolved in 5 ml. of ethanol and this solution was added to a solution of 0.23 g. (0.01 g. atoms) of sodium in 20 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes. The mixture was diluted with water and was acidified with glacial acetic acid. The mixture was extracted with diethyl ether and the ether layer was dried over magnesium sulfate, filtered and was acidified with an etheral hydrochloric acid solution. The mixture was filtered and the filtrate was evaporated. The residue was recrystallized from heptane to give 10 mg. of the title compound, m.p. 110°-112° C.

1. filtrationThe mixture was filtered
2. customthe filtrate was evaporated in a rotary evaporator
3. dissolutionThe residue was dissolved in 5 ml
4. additionof ethanol and this solution was added to a solution of 0.23 g
5. stirringThe mixture was stirred at room temperature for 5 minutes
6. additionThe mixture was diluted with water
7. extractionThe mixture was extracted with diethyl ether
8. dry with materialthe ether layer was dried over magnesium sulfate
9. filtrationfiltered
10. filtrationThe mixture was filtered
11. customthe filtrate was evaporated
12. customThe residue was recrystallized from heptane
13. customto give 10 mg

ORD-Eintrag

ord-216b37b273a94c24813ca62556f22c59

Quelldatensatz

uspto-grants-1980_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04215123