Hydrochloric Acid → HCID 15542694, compound

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)

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 45 minutes
3. waitleft
4. temperaturefor cooling
5. temperaturecooled, to which
6. concentrationconcentrated
7. temperatureA methanol solution (200 ml) of the residue was heated
8. temperatureunder reflux for 6 hours
9. concentrationconcentrated
10. addition3N aqueous sodium hydroxide solution was added to the residue
11. extractionwhich was extracted with ethyl acetate
12. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/10)
13. customThe obtained crude crystals
14. washwere washed with hexane

ORD record

ord-7f884c90f19f44b4819cf5c5d8f169de

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329389B1