2-Nitro-5-phenoxypyridine → 5-Phenoxypyridin-2-amine

HRID 1454916Notes

Reaction equation

HRID 1454916 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][N:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[O:10]([C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[N:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 221794212-Nitro-5-phenoxypyridineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 221794545-Phenoxypyridin-2-amineYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Nitro-5-phenoxy-pyridine (262 mg) was dissolved in dry ethanol (12 mL) and 10% palladium on charcoal (90 mg) was added. A hydrogen atmosphere was introduced by repeated evacuation/hydrogen introduction. The mixture was then allowed to stir for 18 hours. The catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo to give 5-phenoxy-pyridin-2-ylamine (217 mg) as a yellow foam. This material was used without further purification. MS (EI): 186.1 (M+).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-23a1b285be17449ea54836f0b1da727e
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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