Dichloromethane → HCID 59838590, compound

Participants

Reaction Steps

To a flask containing 0.94 g (0.002 mol) of methyl ether N′-(3,5-dimethyl-benzoyl)-N′-(2-methoxy-1,1-dimethyl-ethyl)-hydrazinecarboxylic acid benzyl ester, was added 10 mL of CH2Cl2, 0.87 g of Et3SiH, 0.10 g of palladium acetate, and 1 g of Et3N. The reaction mixture was stirred at room temperature for over 10 hours. More CH2Cl2 (10-20 mL) was added, and the mixture was filtered to remove the palladium. The brown CH2Cl2 solution was treated with MgSO4 and charcoal, then filtered and evaporated. The evaporation yielded 0.87 g of a red, oily solid. TLC indicated the presence of the product: Rf=0.44 in 1:1 ethyl acetate:hexane. The product was purified by chromatography, eluted with 19-20% ethyl acetate/hexane to yield 401 mg (80%) of 3,5-dimethyl-benzoic acid N-(2-methoxy-1,1-dimethyl-ethyl)-hydrazide product. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.1 (s, 2H), 7.0 (s, 1H); 3.682 (s, 2H), 3.377 (s, 3H), 2.319 (s, 6H), 1.495 (s, 3H).

Provenance & Evidence