Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 8-Aminoquinoline | HCID 11359 | — |
| Reactant | HCID 57667966 | HCID 57667966 | — |
| Catalyst | Copper | HCID 23978 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57668103 | HCID 57668103 | 16.3% |
Reaction Steps
To N,N-dimethylformamide 8.8 mL solution of 2-iodo-4-phenoxybenzoic acid 0.88 g were added quinolin-8-amine 0.75 g, N-methylmorpholine 0.85 mL, copper(I) iodide 0.15 g and copper powder 49 mg, and it was stirred at 90° C. for 6 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it, it was adjusted to pH6.5 with 10% citric acid aqueous solution, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to give 4-phenoxy-2-(quinolin-8-ylamino)benzoic acid 0.15 g of pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08327467B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-d488b13482564bcbb3682ebd9a0a7ef2 |
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| Source note | uspto-grants-2012_12 |
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