Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Ethyl 3,6-dichloropyridine-2-carboxylate | HCID 45278327 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 84819635 | HCID 84819635 | 26.8% |
Reaction Steps
To a solution of 3,6-dichloropicolinic acid ethyl ester (5.0 g, 24 mmol) in CH3CN (45 mL) was added NaI (10 g, 66.7 mmol) and acetyl chloride (2.5 mL). The reaction mass was heated in a sealed tube at 100° C. for 48 h. The reaction mass was diluted with EtOAc and was washed with saturated solutions of Na2S2O3 and NaHCO3. The organic layer was separated, dried, filtered and concentrated to afford 2 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.04 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.7 Hz, 1H), 4.38 (q, J=7.5 Hz, 2H), 1.32 (t, J=6.9 Hz, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09006257B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-1740d887c8be4c6d890c509bbc2220f4 |
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| Source note | uspto-grants-2015_04 |
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