Hydrochloric Acid → HCID 18332965, compound

HRID 2269741Notes

Reaction equation

HRID 2269741 reaction equation
C1COCC1.[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=O)[CH:11]([C:18]([N:20]([CH3:22])[CH3:21])=O)[CH2:10]2.Cl>O>[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH2:12][CH:11]([CH2:18][N:20]([CH3:22])[CH3:21])[CH2:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18333007HCID 18333007, compound

Product 1

HCID 18332965HCID 18332965, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1M Borane/THF complex (33 ml) was added to a THF (300 ml) suspension of 6-chloro-N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide (2.135 g). The reaction mixture was heated under reflux for 6 hours, and left standing for cooling. The reaction mixture was ice-cooled, to which was added water (5 ml) and 6N hydrochloric acid (30 ml). The mixture was stirred at room temperature for 15 hours, then concentrated. 3N aqueous sodium hydroxide solution was added to the residue to make basic, which was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/4). The obtained crude crystals were washed with hexane to obtain the entitled compound (1.432 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 hours
  3. waitleft
  4. temperaturefor cooling
  5. temperaturecooled, to which
  6. concentrationconcentrated
  7. addition3N aqueous sodium hydroxide solution was added to the residue
  8. extractionwhich was extracted with ethyl acetate
  9. washThe organic layer was washed with water
  10. dry with materiala saturated aqueous sodium chloride solution, then dried
  11. concentrationconcentrated
  12. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/4)
  13. customThe obtained crude crystals
  14. washwere washed with hexane

Sources & evidence

ORD record
ord-d1b4a6d51915437d84e3879f02c340a7
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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