Ethyl Acetate → 6-Phenoxy-3-pyridinamine

HRID 347678Notes

Reaction equation

HRID 347678 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)([O-])=O.C(OCC)(=O)C>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 32523715-Nitro-2-phenoxypyridine

Product 1

HCID 2128566-Phenoxy-3-pyridinamineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Nitro-6-phenoxypyridine (8.77 g, 40.6 mmol), 10% palladium on carbon (1.20 g) and 1:1 mixed solvent (250 mL) of ethyl acetate with ethanol were mixed and hydrogenation was performed at room temperature under an initial pressure of 196 kPa. After the catalyst was removed by filtration and washed with ethanol, the filtrate was concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v) to obtain 6.50 g (86%) of the title compound as faintly yellow needle-like crystals.

Workup

  1. customwas performed at room temperature
  2. customAfter the catalyst was removed by filtration
  3. washwashed with ethanol
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v)

Sources & evidence

ORD record
ord-9f20b8e9516548a1b233845367cdbb6f
Source dataset
uspto-grants-2007_02
Patent number
US07176204B2

Reaction notes

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