HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 19592364, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Quinoline, 3-bromo-8-nitro- | HCID 79286 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 19592364 | HCID 19592364 | 65.5% |
Reaction Steps
A mixture of 3-bromo-8-nitroquinoline (300 mg), trimethylsilylacetylene (140 mg), palladium (II) chloride (38 mg), catalytic amount of copper (I) iodide, triethylamine (3 ml) and triphenylphosphine (113 mg) in acetonitrile (3 ml) was stirred for 3 hours at ambient temperature. The mixture was diluted with diethyl ether, and insoluble material was filtered off. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate) to give 8-nitro-3-(trimethylsilylethynyl)quinoline (210 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06008230 |
| Source dataset | uspto-grants-1999_12 |
| ORD ID | ord-55bcaa7bf66a4f86b38b541b162c6064 |
| Source note | uspto-grants-1999_12 |