反应详情

温度

90 °C

The title compound was prepared by General Method 1. Triethylamine (13.0 mL, 94.5 mmol) was added dropwise to p-tolylhydrazine hydrochloride (5.0 g, 31.5 mmol) over a period of 5-min. The reaction mixture was stirred for additional 10 min. 5-(2-bromoethyl)-2-methylpyridine (6.3 g, 31.5 mmol) was added dropwise at 25° C. over a period of 10-15 min. The reaction mixture was stirred at RT for 1 h and the subsequently heated at 90° C. for 2-3 h at which point the reaction was found complete by TLC and LC-MS. Reaction mixture was concentrated under reduced pressure and diluted with water (50 mL) and extracted with ethyl acetate (100 mL×2). The organic layer was separated, dried (Na2SO4) and concentrated to obtain crude product as dark brown oil (16.7 g). Purification of crude product by column chromatography (silica gel, 100-200 mesh, eluent: 0-40% ethyl acetate-Hexane) furnished 1.92 g of pure product as brown liquid. Yield: 25%.

1. stirringThe reaction mixture was stirred at RT for 1 h
2. customReaction mixture
3. concentrationwas concentrated under reduced pressure
4. additiondiluted with water (50 mL)
5. extractionextracted with ethyl acetate (100 mL×2)
6. customThe organic layer was separated
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customto obtain crude product as dark brown oil (16.7 g)