Ethanol → 4-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

HRID 387694

Reaction equation

HRID 387694 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)#[N:2].[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([C:1]#[N:2])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 229363416-Cyano-7-(2-methoxyethoxy)-4-(4-nitrophenoxy)quinoline

Product 1

HCID 229365064-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinolineYield 72.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

6-Cyano-7-(2-methoxyethoxy)-4-(4-nitrophenoxy)quinoline (1.8 g), iron (1.8 g) and ammonium chloride (3.6 g) were suspended in an ethanol (30 ml)-water (7 ml) mixed solvent and the suspension was heated and stirred at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was filtered with celite and washed in ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate and concentrated. The obtained solid was washed with ether and dried to obtain 1.2 g of the title compound.

Workup

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washThe obtained solid was washed with ether
  10. customdried

Sources & evidence

ORD record
ord-fa30f18fc7a94ccbb6877e7078efd6e9
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Linked notes

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