Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | MeOH tetrahydrofuran | HCID 21899815 | — |
| Reactant | HCID 59718769 | HCID 59718769 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59718745 | HCID 59718745 | 83.7% |
Reaction Steps
2M sodium hydroxide solution (7.9 mL, 15.8 mmol) was added to a methanol/THF (7.9 mL/7.9 mL) solution of ethyl 1-benzyl-6-ethyl-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (AA06, 1.92 g, 6.3 mmol), which had been obtained in Example 6, at room temperature and stirred at the same temperature for 2 hours. The reaction mixture was diluted with water (10 mL) and washed with ether (20 mL). 2M hydrochloric acid (8 mL, 16 mmol) was added to the water layer and the obtained mixture was extracted with ethyl acetate (20 mL) two times. The organic layer was washed with water (20 mL) two times and then dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and yellow oily 1-benzyl-6-ethyl-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (AA07, 1.43 g) was obtained. The product was let alone for a night and was crystallized. The crystal was recrystallized from ethyl acetate and a white columnar crystal (AA07, 1.00 g, 58.5%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178681B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-51b3ea18ec1a40dc9c5cc8327ce5416e |
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| Source note | uspto-grants-2012_05 |
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