Hydrochloric Acid → HCID 18332991, compound

HRID 2269744Notes

Reaction equation

HRID 2269744 reaction equation
C1COCC1.[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([C:18]([N:20]([CH3:22])[CH3:21])=O)[C:13](=O)[NH:14]2)=[CH:9][CH:8]=1.Cl>O>[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH2:18][N:20]([CH3:22])[CH3:21])[CH2:13][NH:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18333102HCID 18333102, compound

Product 1

HCID 18332991HCID 18332991, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1M Borane/THF complex (80 ml) was added to a THF (180 ml) suspension of 7-chloro-N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide (5.055 g). The reaction mixture was heated under ref lux and left standing for cooling. The reaction mixture was ice-cooled, to which was added water (5 ml) and 6N hydrochloric acid (50 ml). The mixture was stirred at room temperature for one hour, then concentrated. A methanol solution (100 ml) of the residue was heated under reflux for 75 minutes and then concentrated. 3N Aqueous sodium hydroxide solution was added to the residue to make basic, which was extracted with ethyl acetate. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/4). The obtained crude crystals were washed with hexane to give the entitled compound (3.991 g).

Workup

  1. temperatureThe reaction mixture was heated under ref lux
  2. waitleft
  3. temperaturefor cooling
  4. temperaturecooled, to which
  5. concentrationconcentrated
  6. temperatureA methanol solution (100 ml) of the residue was heated
  7. temperatureunder reflux for 75 minutes
  8. concentrationconcentrated
  9. addition3N Aqueous sodium hydroxide solution was added to the residue
  10. extractionwhich was extracted with ethyl acetate
  11. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/4)
  12. customThe obtained crude crystals
  13. washwere washed with hexane

Sources & evidence

ORD record
ord-8a5914f105aa4d148144e697c48e3d15
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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