HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Methyl 4'-[[3-butyl-4-quinolinyl]-methyl](1,1'-biphenyl)-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Methyl 4-(bromomethyl)(1,1'-biphenyl)-2-carboxylate | HCID 19595328 | — |
| Reactant | 3-Butyl-4-chloro quinoline | HCID 19595352 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | Methyl 4'-[[3-butyl-4-quinolinyl]-methyl](1,1'-biphenyl)-2-carboxylate | HCID 19595364 | — |
Reaction Steps
475 mg of electrolytic zinc, 275 mg of tetrakis (triphenylphosphine) palladium, 2.08 g of methyl 4-(bromomethyl)-1,1-biphenyl -2-carboxylate (prepared in EP 0,025,331)) were introduced into 13 ml of tetrahydrofuran. 503 mg of 3-butyl-4-chloro quinoline of Step F were introduced and the mixture was stirred for 15 hours in an ultrasonic bath, allowing the temperature to rise to 65° C. 50 ml of 0.1N hydrochloric acid were added and extraction was carried out with ethyl acetate. The extracts were washed with a saturated solution of sodium chloride, dried and evaporated to dryness. After chromatography on silica (eluant: chloroform-hexane-ethyl acetate 100-100-10), 624 mg of the expected product were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06004979 |
| Source dataset | uspto-grants-1999_12 |
| ORD ID | ord-c846b5dc4ab54752a357bed6ad1ff2fd |
| Source note | uspto-grants-1999_12 |