HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione → 5-Cyano-2-hydroxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione | HCID 22623971 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Pd barium sulfate | HCID 16218511 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Cyano-2-hydroxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione | HCID 22623978 | 45.9% |
Reaction Steps
A mixture of 2-benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.16 g, 0.40 mmol, from Example D2) and 5% Pd/BaSO4 (0.05 g) in THF (75 mL) was shaken in an atmosphere of hydrogen at 50 psi at ambient temperature for 86 hours with an additional 0.05 g of 5% Pd/BaSO4 being added after 70 hours. The catalyst was removed by filtration and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica using chloroform/methanol (10:1) to give 0.059 g of the title compound, mp>250° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06177423B1 |
| Source dataset | uspto-grants-2001_01 |
| ORD ID | ord-a467c954938b41d38cb0c101ad535a32 |
| Source note | uspto-grants-2001_01 |