2'-Hydroxy-5'-methyl-3'-nitroacetophenone → 1-(3-Amino-2-hydroxy-5-methylphenyl)ethan-1-one
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[C:5]([OH:11])=[C:4]([N+:12]([O-])=O)[CH:3]=1>C(O)C.[Pt]>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[C:5]([OH:11])=[C:4]([NH2:12])[CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2-hydroxy-5-methyl-3-nitroacetophenone [4.0 g; Joshi et al., J. Amer. Chem. Soc., (1954), 76, 4993] in ethanol (150 ml) was hydrogenated at 25° C. and 3.5 kg/cm2 for 44 minutes using a catalyst of platinum on charcoal. The solution was filtered and the filtrate was evaporated at 30° C. under diminished pressure to give a dark red oil, which set to a semi-solid on standing overnight. This material was purified by chromatography on a column of silica gel using diethyl ether as eluant. The fastest running band (yellow) was collected to give 3-amino-2-hydroxy-5-methylacetophenone (2.3 g), m.p. 56°-58° C., in the form of a bright yellow solid.