Ethanol → Ethyl(E)-3-[2-amino-4-(4-aminophenoxy)-3-pyridyl]-propenoate

HRID 1433451Notes

Reaction equation

HRID 1433451 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+].CN(C)C=O.C(O)C>[Fe].O>[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([O:15][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 58931221Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate

Product 1

HCID 58931285Ethyl(E)-3-[2-amino-4-(4-aminophenoxy)-3-pyridyl]-propenoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Ethyl (E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate (350 mg), iron powder (700 mg), ammonium chloride (1.4 g), dimethylformamide (7 ml), ethanol (2 ml) and water (2 ml) were stirred at 100° C. for 20 minutes. The mixture was filtered with celite, and then water and ethyl acetate were added for extraction. The organic layer was washed 5 times with aqueous ammonium chloride solution and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 230 mg of the target substance as a light yellow solid.

Workup

  1. filtrationThe mixture was filtered with celite
  2. additionwater and ethyl acetate were added for extraction
  3. washThe organic layer was washed 5 times with aqueous ammonium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain 230 mg of the target substance as a light yellow solid

Sources & evidence

ORD record
ord-fff7a9c185b548198e51e5bd8831feb0
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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