Ammonium Chloride → 4-(5,7-Dimethoxyquinolin-4-yloxy)phenylamine

HRID 573416Notes

Reaction equation

HRID 573416 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1)=[CH:6][CH:7]=[N:8]2.[Cl-].[NH4+]>CO.[Zn]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)=[CH:6][CH:7]=[N:8]2

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 895814265,7-Dimethoxy-4-(4-nitrophenoxy)quinoline

Product 1

HCID 895807364-(5,7-Dimethoxyquinolin-4-yloxy)phenylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5,7-dimethoxy-4-(4-nitrophenoxy)quinoline (50 mg, 0.15 mmol), Zn dust (100 mg, 1.50 mmol) and ammonium chloride (32 mg, 0.60 mmol) in methanol (3 mL) was heated at reflux for 1 h. The mixture was filtered through celite and washed with CHCl3. The organic layer was washed with 10% NaOH solution and brine, dried over Na2SO4, and concentrated to afford 4-(5,7-dimethoxyquinolin-4-yloxy)phenylamine as an off white solid. LCMS m/z=298 (M+1); 1H NMR (CDCl3) δ: 8.44 (d, 1H, J=4.8 Hz), 7.00 (s, 1H), 6.83 (d, 2H, J=8.8 Hz), 6.65-6.63 (m, 3H), 6.32 (d, 1H, J=4.8 Hz), 5.11 (br s, 2H), 3.89 (s, 3H), 3.86 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. filtrationThe mixture was filtered through celite
  4. washwashed with CHCl3
  5. washThe organic layer was washed with 10% NaOH solution and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bfd2d8e1b0b048cca9a23c2f18e3288d
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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