HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 10496423, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Bromobutyryl chloride | HCID 70225 | — |
| Reactant | HCID 10749820 | HCID 10749820 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 10496423 | HCID 10496423 | 7.9% |
Reaction Steps
To a mixture of methyl (E)-3-(6-aminopyridin-3-yl)acrylate (700 mg) and triethylamine (477 mg) in dichloromethane (6 ml) was added dropwise 4-bromobutyryl chloride (801 mg) under nitrigen in ice water bath and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated in vacuo. the residue was chromatographed on silica gel eluting with chloroform and purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:1, v/v) to give methyl (E)-3-[6-(4-bromobutyramido)pyridin-3-yl]acrylate (101 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05994368 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-f53457a320494d08a5a732a2eabb625f |
| Source note | uspto-grants-1999_11 |