[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]([OH:9])[C:4](C2C=CC=CC=2)([N:10]=NC2C=CC=CC=2O)[CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([CH3:8])[C:5]=1[OH:9]A mixture of 5.75 g (25 mmoles) of 4-fluoro-6-methyl-2-phenylazophenol (B1) and 1.1 g of 5% Pd/c in ethyl acetate was shaken in a Parr shaker under hydrogen at room temperature for 17.5 hours. The reaction mixture was filtered through celite and the filtrate concentrated to an oil which was purified on silica gel eluting with hexane-ethyl acetate, giving 3.2 g of a white solid: m.p. 97° C. (dec).
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