Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | HCID 59443490 | HCID 59443490 | — |
| Reactant | HCID 178418300 | HCID 178418300 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59443458 | HCID 59443458 | 74% |
Reaction Steps
3-Methoxy-7-(3-methoxyphenyl)-2-naphthoic acid (323 mg, 1.05 mmol, 1 eq), EDCI (1 eq) and hydroxybenzotriazole (1 eq) are dissolved in 50 ml of dichloromethane. To this solution, cooled at 0° C., are added dropwise methylamine (1 eq) and triethylamine (1 eq) in 40 ml of dry dichloromethane. The reaction mixture is boiled under reflux for 1.5 h, and after cooling, the reaction is stopped by adding 20 ml of 0.1 M HCl. The organic phase is separated, washed with saturated sodium carbonate and chloride solutions, dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. Purification by column chromatography with hexane/ethyl acetate 8/2 as the eluent yielded the desired product in a yield of 74%, 250 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546392B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-f2264dcab60d4e7bbc3f168da954b256 |
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| Source note | uspto-grants-2013_10 |
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