Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 6-Aminophthalide | HCID 93631 | — |
| Reactant | Pyridinium chloride | HCID 10176127 | — |
| Reactant | 4-Chloro-6,7-diethoxyquinoline-3-carbonitrile | HCID 10778872 | — |
| Solvent | 2-Methoxyethanol | HCID 8019 | — |
| Product | HCID 9952290 | HCID 9952290 | 95% |
Reaction Steps
A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile, 230 mg (1.54 mM) of 6-Aminophthalide and 161 mg of pyridine hydrochloride in 12 ml of 2-methoxyethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80° C. to yield 535 mg of 6,7-Diethoxy-4-(3-oxo-1,3-dihydro-isobenzofuran-5-ylamino)-quinoline-3-carbonitrile as a white solid: mass spectrum (electrospray, m/e): M+H 390.1, mp=280-284° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06288082B1 |
|---|
| Source dataset | uspto-grants-2001_09 |
|---|
| ORD ID | ord-b4b9a653e7b64246bce28b66142040a9 |
|---|
| Source note | uspto-grants-2001_09 |
|---|