Water → 6-Chloro-8-aminoquinoline

HRID 987574Notes

Reaction equation

HRID 987574 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[NH4+].[Cl-].O>[Fe].CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 1104626-Chloro-8-nitroquinoline

Product 1

HCID 796186-Chloro-8-aminoquinolineYield 52%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6.30 g (30.3 mmol) 6-chloro-8-nitroquinoline, 14.7 g (272 mmol) NH4Cl, 120 mL H2O and 250 mL EtOH is added 5.0 g (90.6 mmol) Fe powder, and the resulting mixture is refluxed for 2.5 h. The volatiles are evaporated, and the residue is stirred in mixture of 200 mL CH2Cl2 and 300 mL water for 30 min. The resulting bi-phasic solution is filtered through celite, the layers are separated, and the aqueous layer is extracted 2×100 mL CH2Cl2. The combined organics are washed with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography on SiO2, eluting with hexanes/EtOAC (10/1 to 4/1), gives 2.80 g (15.7 mmol, a 52% yield) of the title compound as a tan solid. mp: 70-73° C.; MS (ES) m/z 179 (MH)+.

Workup

  1. temperaturethe resulting mixture is refluxed for 2.5 h
  2. customThe volatiles are evaporated
  3. filtrationThe resulting bi-phasic solution is filtered through celite
  4. customthe layers are separated
  5. extractionthe aqueous layer is extracted 2×100 mL CH2Cl2
  6. washThe combined organics are washed with 1×100 mL H2O, 1×100 mL brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe volatiles are evaporated
  10. washFlash chromatography on SiO2, eluting with hexanes/EtOAC (10/1 to 4/1)
  11. customgives 2.80 g (15.7 mmol

Sources & evidence

ORD record
ord-c367a8c21b9d41398034a9490b803219
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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