Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Clopyralid | HCID 15553 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 28491368 | HCID 28491368 | 53% |
Reaction Steps
3,6 Dichloropyridine-2-carboxylic acid (0.55 g, 2.86 mmol), morpholine (1.37 g, 15.7 mmol) and N,N dimethylacetamide (1.37 mL) were combined and stirred for 24 h at 80° C. An additional volume of morpholine (1.39 g, 15.7 mmol) was added and heating continued for 40 hours more. After cooling the DMA was removed in the presence of toluene. The residue was dissolved in water and extracted with ether to remove excess morpholine. The aqueous was acidified to pH=2 and the product extracted into ether. Crystallization from water gave a white solid, 369 mg (53% yield). 1H NMR (CD3OD): δ 3.52 (t, 4H), 3.78 (t, 4H), 6.97 (d, 1H), 7.65 (d, 1H). LC-MS, M+H: 243.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06956052B2 |
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| Source dataset | uspto-grants-2005_10 |
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| ORD ID | ord-7886a83c144d4cdbaef29f0ad930334d |
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| Source note | uspto-grants-2005_10 |
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