HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → 3-cyclopropylmethyl 5-[2-(N,N-dimethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | 2-(Dimethylamino)ethyl 3-oxobutanoate | HCID 12529170 | — |
| Reactant | Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate | HCID 53956239 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 3-cyclopropylmethyl 5-[2-(N,N-dimethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate | HCID 14100092 | 42.3% |
Reaction Steps
A mixture of 13.0 g (75 mmol) of 2-(N,N-dimethylamino)ethyl acetoacetate, 21.7 g (75 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)-acetoacetate, 6.0 ml of 28% aqueous ammonia and 70 ml of ethanol was stirred at the reflux temperature for 7 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column and crystallized from ethyl ether to afford 3-cyclopropylmethyl 5-[2-(N,N-dimethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (14.1 g, 42.3%) as yellow crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04824855 |
| Source dataset | uspto-grants-1989_04 |
| ORD ID | ord-d1d330aa5135410dae686dc7f283cdd0 |
| Source note | uspto-grants-1989_04 |