HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 7-Bromo-1,2,3,4-tetrahydroisoquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone | HCID 10968831 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 7-Bromo-1,2,3,4-tetrahydroisoquinoline | HCID 10729255 | 60% |
Reaction Steps
A mixture of 7-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydoisoquinoline (G. E. Stokker, Tetrahedron Letters 1996, 37, 5453) (43.4g, 0.14 mol), potassium carbonate (104.3g, 0.75 mol), methanol (1 L) and water (150ml) was heated at reflux for 1 h, then cooled and evaporated in vacuo. Residue was partitioned between water (1 L) and dichloromethane (4×200 ml). Combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil which was dissolved in hexane. The mixture was filtered and the filtrate evaporated in vacuo to give the title compound as an oil (17.7 g, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06465485B1 |
| Source dataset | uspto-grants-2002_10 |
| ORD ID | ord-dbd54edc0e984c06873e7377f3db7e39 |
| Source note | uspto-grants-2002_10 |