Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,2,3,4-Tetrahydro-N,N-dimethyl-2-oxo-3-quinolinecarboxamide | HCID 18333152 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 15542694 | HCID 15542694 | 67.3% |
Reaction Steps
N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide (9.486 g) was added to 1M Borane-THF complex (200 ml). The reaction mixture was heated under reflux for 45 minutes, and left standing for cooling. The reaction mixture was ice-cooled, to which were added water (20 ml) and 6N hydrochloric acid (50 ml). The mixture was stirred at room temperature for 15 hours, and concentrated. A methanol solution (200 ml) of the residue was heated under reflux for 6 hours, and concentrated. 3N aqueous sodium hydroxide solution was added to the residue to become basic, which was extracted with ethyl acetate. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/10). The obtained crude crystals were washed with hexane to give the entitled compound (5.569 g)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06329389B1 |
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| Source dataset | uspto-grants-2001_12 |
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| ORD ID | ord-7f884c90f19f44b4819cf5c5d8f169de |
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| Source note | uspto-grants-2001_12 |
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