Water → HCID 23369739, compound

HRID 1900802Notes

Reaction equation

HRID 1900802 reaction equation
C([N:4]([CH2:8][CH:9]1[O:23][C:12]2=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=[C:11]2[CH:10]1[CH2:24][F:25])[NH:17][C:16](=[O:22])[CH:15]=[CH:14]3)CC=C)C=C.N12CCN(CC1)CC2.O>C(O)C.C(Cl)(Cl)Cl.CO>[NH2:4][CH2:8][CH:9]1[O:23][C:12]2=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=[C:11]2[CH:10]1[CH2:24][F:25])[NH:17][C:16](=[O:22])[CH:15]=[CH:14]3

Participants

7

Reactant 3

HCID 962WaterHCID 9237DabcoHCID 23369595HCID 23369595, compound

Product 1

HCID 23369739HCID 23369739, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

2-Diallylaminomethyl-3-fluoromethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (609.8 mg, 1.78 mmol) was dissolved in ethanol (50 ml). To the solution, Wilkinson catalyst (100.0 mg, 0.108 mmol), 1,4diazabicyclo[2,2,2]octane (100.0 mg, 0.891 mmol) and water (10 ml) were added, and the mixture was refluxed with heat for 90 minutes. The reaction mixture was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: saturated ammonia--methanol=50:1). Pale yellow crude crystals were obtained. The crude crystals were dissolved in a solvent mixture of chloroform and methanol (4:1), to which 1.37N-HCl--methanol solution (1.0 ml, 1.37 mmol) was added. The resultant mixture was condensed under reduced pressure, then subjected to azeotropic distillation along with methanol (twice). The residue was recrystallized from methanol--ethanol--ether. 265.0 mg of the title compound was obtained as pale yellow powdery crystals (49.8%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heat for 90 minutes
  3. customcondensed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform: saturated ammonia--methanol=50:1)
  5. customPale yellow crude crystals were obtained
  6. additionwas added
  7. customcondensed under reduced pressure
  8. distillationsubjected to azeotropic distillation along with methanol (twice)
  9. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-3b38e7e10492450989fda8b43054473a
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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