HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-5-yl)prop-2-enamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 5-Nitroindoline | HCID 36219 | — |
| Reactant | 1H-Indole, 2,3-dihydro-1-methyl-5-nitro- | HCID 167738 | — |
| Solvent | Water | HCID 962 | — |
| Product | (2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-5-yl)prop-2-enamide | HCID 10236808 | — |
Reaction Steps
1-Methyl-5-nitroindoline. To a round-bottomed flask equipped with magnetic stirring was added 5-nitroindoline (0.82, 5.0 mmol, Aldrich), iodomethane (0.71 g, 5.0 mmol, Aldrich), sodium hydroxide (0.24, 6 mmol) and DMF (20 mL). The reaction mixture was stirred at 25° C. for 3 h, diluted with water (50 mL), extracted with EtOAc (3×40 mL) and the combined extracts were concentrated in vacuo. Purification by silica gel chromatography 97:3 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 179 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582657B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-d69981558afe4b55a756cf2deb7ad26b |
| Source note | uspto-grants-2009_09 |