Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 58996249 | HCID 58996249 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 11665862 | HCID 11665862 | 69.8% |
Reaction Steps
A solution of lithium hydroxide (159 mg, 1.27 mmol) in water (6 mL) was added to a solution of methyl 4-amino-3-chloro-6-(1,1-difluroethyl)-pyridine-2-carboxylate (159 mg, 0.63 mmol) in tetrahydrofuran (6 mL). The mixture was vigorously stirred at room temperature overnight and was then concentrated to near dryness. After adding water, the reaction mixture was washed once with ethyl acetate to remove unreacted starting material. The aqueous layer was then acidified to pH<3 with 1N HCl and extracted with ethyl acetate. The organic layer was dried (MgSO4), concentrated and the residue triturated with cold hexane to provide 4-amino-3-chloro-6-(1,1-difluoroethyl)-pyridine-2-carboxylic acid (105 mg, 0.44 mmol) as a white solid; 1H NMR (DMSO-d6): δ 7.02 (s, 1H), 6.94 (br.s, 2H), 1.90 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07291580B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-8785fa3944e243839f9cc3ef1f502889 |
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| Source note | uspto-grants-2007_11 |
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