Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Methyl 2-chloro-6-phenylpyridine-3-carboxylate | HCID 22484962 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 22485195 | HCID 22485195 | 86% |
Reaction Steps
To the mixture of lithium aluminum hydride (120 mg, 2.5 mmol) and tetrahydrofuran (10 ml), a mixture of 2-chloro-6-phenyl-nicotinic acid methyl ester (620 mg, 2.5 mmol) synthesized in Example 24 and tetrahydrofuran (2.4 ml) was gradually added under nitrogen atmosphere at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at the same temperature for 30 minutes. Water was gradually added dropwise thereto at the same temperature, and the obtained reaction mixture was stirred at room temperature for 1 hour. Impurities were removed by filtration with Celite, and the solvents were evaporated under reduced pressure from the filtrate. The obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=2:1), thereby obtaining the entitled compound (470 mg, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273885B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-fefb0ed306bb440197df444b95381c0c |
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| Source note | uspto-grants-2012_09 |
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