Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 12070446 | HCID 12070446 | — |
| Reactant | iodomethane DMF | HCID 86587335 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 12070457 | HCID 12070457 | 97% |
Reaction Steps
To a solution of 5-(4-bromo-2-formyl-N-methylanilino)pentanoic acid (3.0 g) in DMF(8 ml), potassium carbonate (1.6 g) and a solution of methyl iodide/DMF (1.6 g/2 ml) were added at room temperature, and the resulting mixture was stirred for 2 hours. Ethyl acetate and water were added to the mixture, and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated to give yellow oil of 5-(4-bromo-2-formyl -N-methylanilino)pentanoic acid methylester (3.0 g, yield 97%). 1H-NMR(CDCl3, δ, 300 MHz): 1.58-1.64(4H, m), 2.28(2H, t, J=6.8 Hz), 2.83(3H, s), 3.09(2H, t, J=6.8 Hz), 3.63(3H, s), 6.95(1H, d, J=8.8 Hz), 7.51(1H, dd, J=8.8, 2.4 Hz), 7,83(1H, d, J=2.4 Hz), 10.14(1H, s). FAB-MS ([M+Na]+): 350. IR(neat, cm−1): 1735, 1681.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06864367B2 |
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| Source dataset | uspto-grants-2005_03 |
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| ORD ID | ord-a767ca0b01f24c5da278363e781b9358 |
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| Source note | uspto-grants-2005_03 |
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