HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Toluenesulfonyl chloride → 6-Chloro-2-(chloromethyl)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | 6-Chloro-2-methyl-1-oxo-1lambda~5~-quinoline | HCID 15675916 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | 6-Chloro-2-(chloromethyl)quinoline | HCID 12559841 | 54.1% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
6-Chloro-2-methylquinoline N-oxide (1.73 g, 8.1 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (1.7 g, 8.96 mmol) in dichloroethane (80 mL). The reaction mixture was heated to 100° C. overnight under N2, cooled and concentrated, partitioned between 10% K2CO3 /ethyl acetate, dried over MgSO4, and evaporated under reduced pressure to afford a solid. The crude solid was purifed by flash chromatography (4:1 hexane/ethyl acetate) to afford 0.93 g (52%) of pure product as an off white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05084463 |
| Source dataset | uspto-grants-1992_01 |
| ORD ID | ord-6a654d0bf65a47ea935667e45b34b065 |
| Source note | uspto-grants-1992_01 |