HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 80599Generated: October 25, 2026
Cesium carbonate → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
https://huagongshe.com/reaction/80599
Participants
| Role | Name | HCID | Charge |
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| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromo-5-(trifluoromethyl)aniline | HCID 2735880 | — |
| Reactant | 1-(5,6,7,8-Tetrahydroquinolin-8-yl)ethan-1-one | HCID 42604452 | — |
| Reactant | HCID 178418800 | HCID 178418800 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline | HCID 12002825 | 91% |
Reaction Steps
In a pressure tube with one end sealed, add 190 mg CuI (1 mmol), 1.64 g 4-methyl-1H-imidazole (20 mmol), 3.25 g Cs2CO3 (10 mmol), and after Nitrogen replacement, add 2.40 g 3-bromo-5-(trifluoromethyl)aniline (10 mmol), 350 mg 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone (2 mmol) and 30 mL DMF was added into a flask. The mixture was stirred at 110° C. for 18 h under sealing. After cooling to room temperature, the solvent was removed under vacuum and the residue was purified by column chromatography to afford 2.19 g desired product (91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08846671B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-a685fed84c2c492e928d694112f66e81 |
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| Source note | uspto-grants-2014_09 |
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