HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Bromo-3-chloropropane | HCID 8006 | — |
| Reactant | Potassium butoxide | HCID 23699084 | — |
| Reactant | 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline | HCID 135819831 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline | HCID 22048517 | 77.2% |
Reaction Steps
The product of step 2 (206.5 mg, 0.5 mmole) and 1-chloro-3-bromopropane (95 mg, 0.6 mmole) was dissolved in dimethylsulphoxide (5 ml) in the presence of potassium butoxide (0.55 ml, 11.0M in THF, 0.55 mmole) in and the mixture held at room temperature for 18 hours. Water was added and the mixture extracted with ethyl acetate. The combined extracts were washed with water and brine then dried (MgSO4) and evaporated to give 4-(4-(2-methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline (189 mg, 77%) as a yellow gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07402583B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-51ac6b88889046c8b1a1cfe6ffd22062 |
| Source note | uspto-grants-2008_07 |