Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | HCID 117987919 | HCID 117987919 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 117987877 | HCID 117987877 | 69% |
Reaction Steps
A solution of N′-cyclohexyl-4-iodo-2-methoxynicotinohydrazide (220 mg), L-proline (13.5 mg), potassium carbonate (162 mg) and copper(I) iodide (11.2 mg) in DMSO (6 mL) was stirred overnight under nitrogen atmosphere at room temperature. 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 (1.5 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 (100 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-6b0dff0a0b8146e29834ae53133d8d05 |
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| Source note | uspto-grants-2016_06 |
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