Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | HCID 117987881 | HCID 117987881 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 117987863 | HCID 117987863 | 38.8% |
Reaction Steps
A solution of N′-cyclopentyl-4-iodo-2-methoxynicotinohydrazide (695 mg), L-proline (44.3 mg), potassium carbonate (532 mg) and copper(I) iodide (36.6 mg) in DMSO (18 mL) was stirred under nitrogen atmosphere at room temperature for 5 hr. To the reaction mixture was added water under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was removed, to the obtained aqueous layer was added 1N hydrochloric acid (7 mL) under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (174 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09371320B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-05ae51e4c7ce46ccb65f8c747970de2d |
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| Source note | uspto-grants-2016_06 |
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