Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2,4-Dichlorobenzoyl chloride | HCID 66645 | — |
| Reactant | Aluminum(III) Chloride | HCID 6451240 | — |
| Reactant | Methyl 3-methyl-1H-indole-6-carboxylate | HCID 21938240 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 21938274 | HCID 21938274 | 77.3% |
Reaction Steps
Aluminium chloride (1.72 g) is suspended in methylene chloride (50 ml), to which are added 2,4-dichlorobenzoyl chloride (1.35 g) and then 6-(methoxycarbonyl)-3-methylindole (1.00 g), and stirred at room temperature for 16 hours and then at 40° C. for 2.5 hours. The reaction mixture is poured into water with ice, and then extracted with ethyl acetate (150 ml). The organic layer is washed three times with a saturated aqueous sodium hydrogencarbonate solution (50 ml) and then with a saturated saline solution, and thereafter dried with anhydrous sodium sulfate. The drying agent is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting crystal is washed with methyl t-butyl ether and dried to obtain 2-(2,4-dichlorobenzoyl)-6-(methoxycarbonyl)-3-methylindole (71) (1.48 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06410584B1 |
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| Source dataset | uspto-grants-2002_06 |
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| ORD ID | ord-48906a2512d04f41a15cae4172751eff |
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| Source note | uspto-grants-2002_06 |
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