Ammonium Chloride → 6-Fluoroquinolin-8-amine

HRID 514825Notes

Reaction equation

HRID 514825 reaction equation
[F: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-]>CCO.O.[Zn]>[F: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

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 154273Quinoline, 6-fluoro-8-nitro-

Product 1

HCID 132279926-Fluoroquinolin-8-amineYield 74.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 6-fluoro-8-nitroquinoline (1.6 g, 8.3 mmol), and NH4Cl (2 g, 41.5 mmol) in EtOH/H2O (10 mL/10 mL) in a round bottom flask equipped with a refluxing condenser was added Zn (5.4 g, 16.6 mmol) dust in portions at room temperature, and the resulting mixture was stirred at 60° C. overnight. The reaction mixture was filtered, and the filtrate was extracted with EtOAc. The combined organic layers were dried over Na2SO4, and concentrated to give 1.0 g of crude product, which was used directly for the next step without further purification. LC-MS: m/z 163.2 (M+H)+

Workup

  1. customequipped with a refluxing condenser
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5211163b9c3e421c9e3b6c5c1aa6c955
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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