Hydrochloric Acid → HCID 17956177, compound

Participants

Reaction Conditions

Reaction Steps

3-Fluoro-4-methylaniline (1.247 g, 9.96 mmol), 3-chloropropionyl chloride (1.269 g, 9.99 mmol), and K2CO3 (1.450 g, 10.5 mmol) in MeCN (10 mL) were stirred at 40° C. for 3 h. The reaction mixture was quenched with 4M HCl and the product extracted into CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue (1.168 g) was heated to 145° C. and small portions of AlCl3 (3.538 g, 26.5 mmol) were added over a period of 30 min. The reaction mixture was then cooled and 4M HCl added under stirring followed by extraction of the product into CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by flash CC (SiO2; CH2Cl2/MeOH 40:1) to give the title compound (97KK40) (0.201 g, total yield 11%). 1H NMR (CDCl3) δ 8.15 (br s, 1H), 6.94 (d, J=7.8 Hz, 1H), 6.47 (d, J=10.0 Hz, 1H), 2.91-2.87 (m, 2H), 2.62-2.60 (m, 2H), 2.19 (d, J=1.8 Hz, CH3).

Provenance & Evidence