Ethanol → (4-Amino-3-ethoxyphenyl)(2-pyridyl)methanol

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[OH:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2].C(OCC)(=O)C.C(O)C>C(O)(=O)C>[NH2:10][C:9]1[CH:8]=[CH:7][C:6]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[OH:14])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

Procedure

To a solution of (3-ethoxy-4-nitrophenyl)(2-pyridyl)methanol (2.5 g) in acetic acid (50 ml), reduced iron (7.5 g) was added to the mixture and the mixture was stirred overnight. Ethyl acetate and ethanol were added to the mixture, and the unnecessary substances were filtered off. The filtrate was concentrated under reduced pressure, the residue was diluted with ethyl acetate and neutralized with an aqueous solution of saturated sodium bicarbonate. The organic layer was separated and washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) and recrystallized from hexane-ethyl acetate, to give (4-amino-3-ethoxyphenyl)(2-pyridyl)methanol (340 mg) as crystals.