Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3'-Amino-N,N-dimethyl[1,1'-biphenyl]-4-carboxamide | HCID 19603290 | — |
| Reactant | HCID 19603383 | HCID 19603383 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Methylquinoline | HCID 7060 | 92.1% |
Reaction Steps
A mixture of 8-[2,6-dichloro-3-(N-methanesulfonyloxyacetyl-N-methylamino)benzyloxy]-2-methylquinoline (110 mg), 4-(3-aminophenyl)-N,N-dimethylbenzamide (60.2 mg) and potassium carbonate (94.2 mg) in N,N -dimethylformamide (1 ml) was stirred for 12 hours at 60° C., and ethyl acetate and water were added thereto. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1, V/V) to give 8-[2,6-dichloro-3-methylamino]benzyloxy]-2-methylquinoline (30 mg) as colorless amorphous.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05994368 |
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| Source dataset | uspto-grants-1999_11 |
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| ORD ID | ord-f06a43aa50bf4e399c3cee4f732cc3e0 |
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| Source note | uspto-grants-1999_11 |
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