Ethanol → 2-Amino-4-(4-aminophenoxy)pyridine

HRID 387922Notes

Reaction equation

HRID 387922 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+].C(O)C.CN(C)C=O>[Fe].O>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Product 1

HCID 229367412-Amino-4-(4-aminophenoxy)pyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

After adding 1 g of 2-amino-4-(4-nitrophenoxy)pyridine to a mixture of 2.0 g of iron powder, 4.0 g of ammonium chloride, 30 ml of ethanol, 30 ml of dimethylformamide and 15 ml of water, the mixture was vigorously stirred at 100° C. for 10 minutes. The reaction solution was filtered with celite and the solvent was distilled off under reduced pressure to obtain 0.53 g of the target substance as a solid.

Workup

  1. filtrationThe reaction solution was filtered with celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain 0.53 g of the target substance as a solid

Sources & evidence

ORD record
ord-75f41c00f57941f3a7e79d4347ae26f3
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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