Cl[CH2:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:4]=1[NH:5][C:6](=[O:9])[CH2:7][Cl:8].C(N(CC)CC)C>C(OCC)(=O)C.[Pd]>[CH3:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[C:4]=1[NH:5][C:6](=[O:9])[CH2:7][Cl:8]A solution of 2.02 g (7.06 mmol) of 2'-(chloromethyl)-6'-(trifluoromethyl)-2-chloroacetanilide and 1.0 ml (7.2 mmol) of triethylamine in 60 ml of ethyl acetate was shaken with 79.8 mg of 10% Pd/C under an initial H2 pressure of 50 psi. After 19 hr., the mixture was filtered and evaporated to give 1.57 g of 2'-methyl-6'-(trifluoromethyl)-2-chloroacetanilide assaying 94.2% (yield 83.3%) and contaminated with 1.3% of overreduced product.
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