HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Ethylcyclopropan-1-amine hydrochloride | HCID 12953698 | — |
| Reactant | 3-Chloro-3-(2-chloropyridin-3-yl)acrylonitrile | HCID 76759593 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile | HCID 76759595 | 57.3% |
Reaction Steps
To a solution of 3-chloro-3-(2-chloropyridin-3-yl)acrylonitrile (1.4 g, 7.03 mmol, 1 eq.) in 15 ml of acetonitrile was added 2-ethylcyclopropanamine hydrochloride (1.02 g, 8.44 mmol, 1.2 eq.) followed by triethylamine (TEA) (1.06 g, 10.55 mmol, 1.5 eq.). The reaction was microwaved (130° C., 2000 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.998 g, 51% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08476197B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-1c51fc11b8234b18ba30d39a2625396c |
| Source note | uspto-grants-2013_07 |