Ammonium Chloride → 7-Methoxyquinolin-6-amine

HRID 1773559Notes

Reaction equation

HRID 1773559 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:13]([O-])=O.[Cl-].[NH4+]>C(O)C.CN(C)C=O.[Fe]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[NH2:13]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 580563217-Methoxy-6-nitro-quinoline

Product 1

HCID 580561357-Methoxyquinolin-6-amineYield 84.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-6-nitro-quinoline (5 g, 24.0 mmol), iron powder (9.8 g, 172 mmol) and ammonium chloride (9.1 g, 172 mmol) in a mixture of ethanol and water (3/1, 160 mL) was heated at reflux overnight. The resulting mixture was filtered through a CELITE™ pad, the filtrate was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (EtOAc) to afford 3.551 g of 7-methoxy-quinolin-6-ylamine as a grey solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationThe resulting mixture was filtered through a CELITE™ pad
  4. customthe filtrate was evaporated under reduced pressure
  5. customthe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-650cb335f23744288303af919bca43f2
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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