Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ethyl 3-hydroxybenzoate | HCID 24522 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloro-5-(chloromethyl)pyridine | HCID 155479 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86651081 | HCID 86651081 | 16% |
Reaction Steps
NaH (55% suspension in mineral oil, 1.2 g, 28 mmol) was slowly added to a suspension of 2-chloro-5-chloromethylpyridine (3.0 g, 19 mmol), ethyl 3-hydroxybenzoate (3.1 g, 19 mmol), and potassium iodide (600 mg, 3.7 mmol) in DMF (20 ml). After stirring for 2 days at 20° C., water (10 ml) and NaOH (32.5%, 2 ml) was added. The dark mixture was stirred at 80° C. overnight, wereupon it was concentrated in vacuo. The residue was purified by preparative LC-MS to give 0.80 g of the title compound. LC-MS (m/z): 264 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08907096B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-ff56d50b12fb4ed08ae2b0693f82670d |
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| Source note | uspto-grants-2014_12 |
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