Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | HCID 22716713 | HCID 22716713 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 12988027 | HCID 12988027 | — |
Reaction Steps
To a 10 ml toluene solution containing 1.00 g of 4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-carboxylic acid were added 900 mg of DPPA and 0.5 ml of triethylamine, followed by heating at an oil bath temperature of 100° C. for 1 hour. Then, 10 ml of ethanol was added thereto and the whole was further stirred under heating for 30 minutes. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (toluene-ethyl acetate) and then recrystallized from ethyl acetate to obtain 590 mg of ethyl N-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]carbamate as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06740662B1 |
|---|
| Source dataset | uspto-grants-2004_05 |
|---|
| ORD ID | ord-93258c598cbb46758e7bdf8b28f3f3cb |
|---|
| Source note | uspto-grants-2004_05 |
|---|