HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfide → 6,7-Dihydro-5H-quinoline-8-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfide | HCID 1068 | — |
| Reactant | Ozone | HCID 24823 | — |
| Reactant | 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline | HCID 54074650 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6,7-Dihydro-5H-quinoline-8-one | HCID 11744777 | 79% |
Reaction Steps
A solution of 8-benzylidene-5,6,7,8-tetrahydro-quinoline (4.30 g, 19.4 mmole) in CH2Cl2 (150 mL) was reacted with ozone at −78° C. for 30 minutes. Dimethyl sulfide (5 mL) was added, and the reaction was warmed to RT and stirred overnight. The mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (EtOAc). The title compound (2.20 g, 79%) was obtained as an off-white solid after drying in vacuo: MS (ES) m/e 148 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07879872B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-499d9cf6002f49eca7a230a4f1f904de |
| Source note | uspto-grants-2011_02 |