Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | [2-(5-Chloropyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid | HCID 19842220 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 19842210 | HCID 19842210 | 26.2% |
Reaction Steps
3-Oxo-2-(5-chloro-2-pyridyl)isoindoline-1-acetic acid (1 g) and triethylamine (0.8 g) were dissolved in 20 ml of dry tetrahydrofuran and, under ice-cooling with stirring, 0.39 g of ethoxycarbonyl chloride was added portionwise. The mixture was stirred for 3 minutes, 0.56 g of piperidine was added, and the whole mixture was stirred for an additional 30 minutes. The reaction mixture was poured into 500 ml of ice water, followed by extraction with ethyl acetate. The extract was washed with water and dried. The ethyl acetate was then distilled off and the residue was treated with ether. The resulting crystals thus obtained were collected by filtration and recrystallized from ethyl acetate to give 0.32 g of colorless crystals, melted at 165°-166° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04590189 |
|---|
| Source dataset | uspto-grants-1986_05 |
|---|
| ORD ID | ord-4b5c12df79034871bd55a84966ecafe2 |
|---|
| Source note | uspto-grants-1986_05 |
|---|