2-Nitro-5-(3-nitrophenoxy)pyridine → 5-(3-Aminophenoxy)pyridin-2-amine

HRID 1874321Notes

Reaction equation

HRID 1874321 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)=[CH:6][N:5]=1)([O-])=O>CO.[C].[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[N:5][CH:6]=1

Participants

4

Reactant 1

HCID 577491152-Nitro-5-(3-nitrophenoxy)pyridine

Product 1

HCID 577491665-(3-Aminophenoxy)pyridin-2-amineYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-5-(3-nitrophenoxy)pyridine (1.33 g, 5.07 mmol) in methanol (10 mL) was added palladium carbon (50% water-containing product, 100 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 12 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure and dried to give the title compound (980 mg, 96%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-a81113a96572486e82148948405ef910
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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