Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Fluoro-3-methoxybenzaldehyde | HCID 2737358 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18763867 | HCID 18763867 | 98% |
Reaction Steps
4-Fluoro-3-methoxybenzaldehyde (500 mg, 3.24 mmol) was dissolved in 6.9 mL of DMSO and 2.8 mL of water, and then potassium carbonate (0.45 g, 3.3 mmol) and dimethylamine solution in ethanol (0.88 mL, 5.5 M, 4.8 mmol) were added to the solution at room temperature, successively. After being stirred at 100° C. for 5 h, the reaction mixture was cooled to room temperature. The reaction mixture was diluted with ethyl acetate, and the solution was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (eluting with hexane/ethyl acetate=4/1 to 2/1) to obtain the title compound as a pale yellow oil (569 mg, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962674B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-763de09bb3ad4654b5fa19fb4fcc7db3 |
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| Source note | uspto-grants-2015_02 |
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