HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Amino-3-chlorophenol | HCID 87184 | — |
| Reactant | Methyl 4-chloro-7-(2-methoxyethoxy)-6-quinolinecarboxylate | HCID 22936872 | — |
| Solvent | Water | HCID 962 | — |
| Product | Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate | HCID 22936947 | — |
Reaction Steps
Methyl 4-chloro-7-(2-methoxyethoxy)-6-quinolinecarboxylate (4.9 g), 4-amino-3-chlorophenol (2.0 g), sodium hydride (550 mg) and dimethylformamide (20 ml) were stirred together at 100° C. for 2 hours. The mixture was returned to room temperature, water was added, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate) to obtain 3.2 g of the target substance as a violet solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07973160B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-078f2e351faa4a31adad38c2df161330 |
| Source note | uspto-grants-2011_07 |