2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine → 2-Amino-4-(4-amino-2-fluorophenoxy)pyridine

HRID 492669Notes

Reaction equation

HRID 492669 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][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.[H][H]>CO.O1CCCC1.[C].[Pd]>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 231533352-Amino-4-(4-amino-2-fluorophenoxy)pyridineYield 107.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine (1.246 g) was dissolved in methanol (20 ml)-tetrahydrofuran (10 ml), and then 10% palladium carbon (1.0 g) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring for 6 days. After replacing with nitrogen inside the system, the catalyst was filtered and washed with ethanol. The filtrate was concentrated under a reduced pressure to provide the titled compound (1.182 g, quantitative) as brown crystals.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-3c3dec5c8eeb4a2c8a8468942c00a77f
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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