Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-Methoxy-4-methylaniline | HCID 27882 | — |
| Reactant | 2-Bromo-1-(1-methylcyclopropyl)ethan-1-one | HCID 12822308 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86703326 | HCID 86703326 | 54.6% |
Reaction Steps
A solution of 3-methoxy-4-methylaniline (2.26 g) in ethanol (7 mL) was heated under reflux while stirring. To the solution was added slowly a solution of 2-bromo-1-(1-methylcyclopropyl)ethan-1-one (885 mg) in ethanol (3 mL), and this mixture was heated under reflux for 3 hours while stirring. The reaction mixture was left to be cooled. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (588 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815903B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-0dc455ee163c456b927f05dbf4691630 |
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| Source note | uspto-grants-2014_08 |
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