[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>C(O)C.[Pd]>[O:10]([C:9]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[NH2:1])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1To a slurry of 10% Pd/C in 5 ml of absolute ethanol was added 3-nitro-4-phenoxypyridine (7.5 g) in 245 ml of ethanol. This mixture was shaken on a Parr apparatus for two hours. The mixture was filtered and the filtrate concentrated to yield an oil (6.4 g) which was eluted with ethyl acetate on a silica gel column in HPLC. The desired fractions were concentrated to yield an oil (4.5 g). This material was distilled using a Kugelrohr apparatus to yield an oil (1.8 g).
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