HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoate → 5-Hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoate | HCID 12171345 | — |
| Reactant | 5-Hydrazinyl-2-methoxypyridine | HCID 22217853 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 5-Hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester | HCID 23143676 | — |
Reaction Steps
4-(2-Pyridyl)-2,4-dioxobutanoic acid ethyl ester (1.10 g) obtained from Referential Example 31 and 5-hydrazino-2-methoxypyridine (0.692 g) obtained from Referential Example 2 were dissolved in ethanol (22 mL). The resultant mixture was refluxed under heat for 14 hours, followed by cooling in air. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), followed by purification through silica gel column chromatography (toluene-acetone), to thereby give 5-hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester as a solid substance (0.575 g, 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07622471B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-170b13e042244dee9a638a215342bbcf |
| Source note | uspto-grants-2009_11 |