HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzaldehyde → 3-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chlorobenzaldehyde | HCID 6996 | — |
| Reactant | 2-Azidoethanol | HCID 123118 | — |
| Reactant | Methyl 3-aminocrotonate | HCID 643918 | — |
| Reactant | Ethyl 4-(2-azidoethoxy)-3-oxobutanoate | HCID 13663141 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 3-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate | HCID 3092606 | 29.9% |
Reaction Steps
Ethyl 4-(2-azidoethoxy)acetoacetate (46.4 g), prepared from 2-azidoethanol similarly to the method described in Preparation 3, was reacted with methyl 3-aminocrotonate (24.8 g) and 2-chlorobenzaldehyde (30.3 g) in methanol (150 ml) at reflux for 18 hours. After cooling to room temperature, the resulting solid was collected, washed twice with methanol and dried to give the title compound (28 g). The product could be crystallised from methanol, acetone or ethyl acetate. It was used directly.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04572909 |
| Source dataset | uspto-grants-1986_02 |
| ORD ID | ord-1898d73dc9674d45a98388837ce7fd60 |
| Source note | uspto-grants-1986_02 |