Ammonium Hydroxide → 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-phenylmethyl-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid, 2-(N-benzyl-N-methylamino)ethyl ester

A mixture of 15.2 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 13.1 g. of o-trifluoromethylbenzaldehyde, 18.7 g. of 2-(N-benzyl-N-methylamino)ethyl acetoacetate, 6 ml. of 28% ammonium hydroxide and 200 ml. of isopropanol was heated at reflux for 3 hours. The solution was evaporated to dryness. The residue was dissolved in 100 ml. of methylenechloride and extracted with 150 ml. of 15% hydrochloric acid. The acid extract was cooled and made basic with saturated sodium carbonate solution. The mixture was extracted with methylenechloride. The methylenechloride solution was dried over magnesium sulfate, then evaporated in vacuo to a solid residue. The residue was recrystallized from ethanol to obtain the title compound, m.p. 183°-185° C.

1. additionA mixture of 15.2 g
2. temperatureat reflux for 3 hours
3. customThe solution was evaporated to dryness
4. dissolutionThe residue was dissolved in 100 ml
5. extractionof methylenechloride and extracted with 150 ml
6. extractionThe acid extract
7. temperaturewas cooled
8. extractionThe mixture was extracted with methylenechloride
9. dry with materialThe methylenechloride solution was dried over magnesium sulfate
10. customevaporated in vacuo to a solid residue
11. customThe residue was recrystallized from ethanol

ORDレコード

ord-7165624d800142b3b136e0fa8e6bdd51

出典データセット

uspto-grants-1982_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04321384