HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzocaine → ethyl 4-(pyridine-3-carbonylamino)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzocaine | HCID 2337 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Pyridinecarbonyl chloride, hydrochloride (1:1) | HCID 88438 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | ethyl 4-(pyridine-3-carbonylamino)benzoate | HCID 279888 | 85.1% |
Reaction Steps
A mixture of 1.83 g (0.01 mol) of nicotinoyl chloride hydrochloride (97%), 1.65 g of (0.01 mol) of ethyl 4-aminobenzoate, 2.22 g (0.022 mol) of triethylamine and 61 mg of 4-dimethylaminopyridine in 33 ml of dichloromethane is refluxed 24 hours. The solution is washed with water, 2N citric acid and NaHCO3 solution. The solvent is removed and the residue triturated with methanol to give 2.3 g of ethyl 4-[(3-pyridinylcarbonyl)amino]benzoate as yellow crystals, m.p. 125°-127° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05686445 |
| Source dataset | uspto-grants-1997_11 |
| ORD ID | ord-5077a75c3b0c4661ba1a92a813e5c735 |
| Source note | uspto-grants-1997_11 |