HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Isopropyl 5-cyano-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 2-Butenoic acid, 3-amino-, 1-methylethyl ester | HCID 11137274 | — |
| Reactant | 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde | HCID 57438889 | — |
| Reactant | Sodium 1-cyanoprop-1-en-2-olate | HCID 74083625 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | Isopropyl 5-cyano-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate | HCID 66991696 | — |
Reaction Steps
A solution of 100 mg (0.45 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 46.9 mg (0.45 mmol) of sodium 1-cyanoprop-1-en-2-olate, 63.88 mg (0.45 mmol) of isopropyl 3-aminocrotonate and 0.04 ml (0.67 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over sodium sulfate and concentrated. The resulting residue is crystallized from diethyl ether. The beige-colored crystals are filtered off with suction and dried at 40° C. in a vacuum drying oven. 105.9 mg (57.3% of theory) of the title compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08058447B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-b7b10c226ae54a7f9603c8ea8576edf2 |
| Source note | uspto-grants-2011_11 |