HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoyl chloride → HCID 86659859, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-methoxy-2,3-dihydro-1H-indole | HCID 10701974 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86659859 | HCID 86659859 | 65.5% |
Reaction Steps
To a solution of 5-methoxyindoline (202 mg, 1.35 mmol) and N,N-diisopropylethylamine (0.34 mL, 2.0 mmol) in 4.0 mL of dry dichloromethane was added benzoyl chloride (0.23 mL, 2.0 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 70/30) to obtain 5-methoxy-1-benzoylindoline (224 mg, 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08686024B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-91e5c1a183de46128b4233682c74472b |
| Source note | uspto-grants-2014_04 |