HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 1,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 2-Methylbenzaldehyde | HCID 10722 | — |
| Reactant | Methyl 3-aminocrotonate | HCID 643918 | — |
| Reactant | 1-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one | HCID 12900692 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | 1,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester | HCID 12818455 | — |
Reaction Steps
A mixture of 6.1 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 3.6 g. of methyl-3-aminocrotonate (97%), 3.6 g. of o-tolualdehyde, 55 ml. of ethanol and 18 ml. of acetic acid was refluxed for 7 hours. The solution was evaporated to dryness in vacuo. The residue was triturated with diethyl ether and the solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 201°-204° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04321384 |
| Source dataset | uspto-grants-1982_03 |
| ORD ID | ord-54200fc560884c8bb698f0b19a1e03a8 |
| Source note | uspto-grants-1982_03 |