Ethanone, 1-[2-(methylamino)phenyl]- (9CI)

To an oven-dried round-bottomed flask containing K2CO3 (3.46 g, 25 mmol, 1 equiv) suspended in anhydrous DMF (15 mL), was added 1-(2-aminophenyl)ethan-1-one (3.04 mL, 25 mmol) under argon atmosphere and reaction mixture was stirred at RT for 15 min. A solution of MeI (1.56 mL, 25 mmol, 1 equiv) in anhydrous DMF was added dropwise to the reaction mixture. The reaction mixture was stirred at RT for 3 days. The reaction mixture was diluted with H2O (60 mL) and extracted with ethyl acetate (340 mL). The combined organic phases were washed with water (50 mL) and brine (50 mL) and dried over anhydrous sodium sulfate. The filtered olution was concentrated in vacuo and purified by column chromatography (3percent-5percent ethyl acetate in petroleum ether) to yield 1-(2-(methylamino)phenyl)ethan-1-one (1.98 g, 53percent) as yellow crystals. To an oven-dried high-pressure sealed tube was added 1-(bromomethyl)-2-iodobenzene (1.48 g, 5 mmol), 1-(2-(methylamino)phenyl)ethan-1-one (895 mg, 6 mmol, 1.1 equiv), K2CO3 (1.38 g, 10 mmol, 2 equiv) and acetonitrile (5 mL). The reaction mixture was stirred at 85° C for 4 days. The reaction mixture was cooled to RT, diluted with H2O (20 mL) and extracted with dichloromethane (315 mL). The combined organic phases were washed with brine (40 mL) and dried over anhydrous sodium sulfate. The filtered solution was concentrated in vacuo and purified by column chromatography (5percent ethyl acetate in petroleum ether) to yield 1-(2-((2-iodobenzyl) (methyl)amino)phenyl)ethan-1-one 44 (1.45 g, 79percent) as orange crystals;General procedure: Substrate (0.5 mmol) and 11 (0 or 0.1 equiv) were added to a pressure tube. Base and anhydrous solvent were added into the tube in the glove box. The tube was then sealed properly and then removed from the glove box. The reaction was carried out at the given temperature for the given reaction time. The reaction was stopped and the pressure tube was cooled to RT. The reaction mixture was quenched with either water or saturated aqueous ammonium chloride (20 mL) and extracted with diethyl ether or dichloromethane or ethyl acetate (320 mL). The combined organic layers were then washed with water (15 mL) and brine(15 mL) and dried over anhydrous sodium sulfate. The filtered solution was concentrated in vacuo and purified by column chromatography to yield products.

Molecular Weight:149.19
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:149.084063974
Monoisotopic Mass:149.084063974
Topological Polar Surface Area:29.1
Heavy Atom Count:11
Complexity:145
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes