Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Pivaloyl chloride | HCID 62493 | — |
| Reactant | 2-Aminonicotinic acid | HCID 72930 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57867428 | HCID 57867428 | 81.3% |
Reaction Steps
To a mixture of 2-aminonicotinic acid (13.8 g, 100 mmol), 4-dimethylaminopyridine (1.2 g, 10 mmol), triethylamine (55.8 mL, 400 mmol) and N-methylpyrrolidone (140 mL, 42 mmol) was added pivaloyl chloride (24.1 g, 200 mmol) dropwise at 0° C., and after the drop wise addition was finished, which was stirred overnight at room temperature. To the reaction mixture was added water, extracted with toluene, and the organic layer was washed with water and saturated sodium chloride water. After the solution was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under a reduced pressure. To the residue was added n-heptane, which was suspended and stirred at 0° C., which was filtered, so as to obtain the title compound (16.6 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08410277B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-8275402d17ce45a280ddbd6fc797e6d1 |
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| Source note | uspto-grants-2013_04 |
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