Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-(Trifluoromethyl)benzaldehyde | HCID 67990 | — |
| Reactant | Methyl 3-aminocrotonate | HCID 643918 | — |
| Reactant | HCID 12529176 | HCID 12529176 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 12529148 | HCID 12529148 | — |
Reaction Steps
In 3 ml. of isopropyl alcohol were dissolved 1.07 g. of acetoacetic acid β-(N-methyl-N-p-methylbenzylamino)ethyl ester, 0.466 g, of β-aminocrotonic acid methyl ester, and 0.705 g. of m-trifluoromethyl benzaldehyde and the solution was refluxed for 6 hours. The reaction mixture was concentrated, subjected to a silica gel column chromatography (diameter 4 cm, height 15 cm.), and then the effluents containing the aimed product obtained were collected and concentrated. The residue thus obtained was dissolved in acetone and after adjusting the solution to pH 1-2 with an ethanol solution saturated with hydrogen chloride, the solution was concentrated. Then, by crystallizing the residue formed with acetone, 0.8 g. of 2,6-dimethyl-4-(3'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-β-(N-methyl-N-p-methylbenzylamino)ethyl ester hydrochloride was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US03985758 |
|---|
| Source dataset | uspto-grants-1976_10 |
|---|
| ORD ID | ord-596f14ed29b544a3bdcc804dc5a38370 |
|---|
| Source note | uspto-grants-1976_10 |
|---|