HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Hydrochloric Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 7-nitro-9H-indeno[2,1-b]pyridine | HCID 12634294 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Adams' catalyst | HCID 345198 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Hydrochloric Acid | HCID 313 | — |
| Product | cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-7-ylamine | HCID 58294569 | — |
Reaction Steps
A mixture of 7-nitro-9H-indeno[2,1-b]pyridine (3.25 g), 10% palladium on carbon (0.35 g), and methanol (50 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 22 h. PtO2 (0.50 g) and 4 M aqueous hydrochloric acid (3.2 mL) are then added and shaking is continued under hydrogen atmosphere (1 bar) at room temperature for another 22 h. The catalysts are separated by filtration and the filtrate is concentrated to give the crude title compound as its hydrochloric acid salt that is used without further purification or transformed to the free base by treatment with aqueous NaOH solution and extraction into ethyl acetate. Yield: 4.20 g (ca. 80% pure); LC (method 1): tR=0.52 min; Mass spectrum (ESI+): m/z=189 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08497281B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-de495d2aad84489d9790c5fa71366e89 |
| Source note | uspto-grants-2013_07 |