Ethyl Acetate → 6-Phenoxy-3-pyridinamine

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

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.