Ammonium Chloride → 4-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

HRID 1517882Notes

Reaction equation

HRID 1517882 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 114507634-(2-Fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline

Product 1

HCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline (16.0 g, 0.046 mol) and NH4Cl (6.0 g, 0.11 mol) in EtOH/H2O (150 mL, v/v=4:1) was added iron powder (12.4 g, 0.22 mol) at rt. The reaction mixture was heated to reflux for 2 h, then cooled down to rt. Celite (10 g) was then added and stirring for 30 min. The mixture was filtered and the solid was washed with MeOH (20 mL×3) and DCM (20 mL×3). The filtrate was washed with 30 mL of saturated NaHCO3 aqueous. The aqueous phase was extracted with DCM (20 mL×3). The combined organic phases were washed with brine (20 mL×3), dried over Na2SO4, and concentrated in vacuo to give a yellow solid (0.9 g, 98%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. additionCelite (10 g) was then added
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with MeOH (20 mL×3) and DCM (20 mL×3)
  6. washThe filtrate was washed with 30 mL of saturated NaHCO3 aqueous
  7. extractionThe aqueous phase was extracted with DCM (20 mL×3)
  8. washThe combined organic phases were washed with brine (20 mL×3)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-729ad86cb87247d48fca9da94478e927
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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