Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Pyridinecarbonyl chloride, hydrochloride (1:1) | HCID 88438 | — |
| Reactant | HCID 15711966 | HCID 15711966 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 15766689 | HCID 15766689 | 16.9% |
Reaction Steps
5.34 g of nicotinic acid chloride hydrochloride was suspended in 50 ml of methylene chloride and 7.56 g of triethylamine was added thereto. After the resulting suspension was stirred at room temperature for 30 minutes, 3.88 g of 6-chloro-2,2-dimethyl-1,2-dihydroquinoline dissolved in 20 ml of methylene chloride was added thereto. Further, 1.00 g of 4-dimethylaminopyridine was added thereto. After refluxing the resulting solution mixture for 7 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer separated from the aqueous layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was subjected to thin-layer chromatography (silica gel; ethyl acetate/hexane 1:1 (V/V)) to obtain 1.01 g of 6-chloro-2,2-dimethyl-1-nicotinoyl-1,2-dihydroquinoline (the present compound (1)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05354729 |
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| Source dataset | uspto-grants-1994_10 |
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| ORD ID | ord-8e0c4ffc8f1d4c96b0c1b21292c5039c |
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| Source note | uspto-grants-1994_10 |
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