N-(3-amino-4-methylphenyl)acetamide → HCID 67271594, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-amino-4-methyl-phenyl)acetamide (5 g, 25 mmol) in DMF (5 mL) was added 2-chloropyrimidine (3.8 g, 33 mmol) and KI (0.5 g). The reaction was stirred at 100° C. overnight, cooled to 10° C. (100 mL). The resulting mixture was extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuum. The residue was dissolved in conc. HCl (10 mL), stirred at 80° C. for 2 h and concentrated under vacuum to yield 6-methyl-N′-(pyrimidin-2-yl)benzene-1,3-diamine hydrochloride (3.75 g, 75% yield). 1H NMR (400 MHz, CDCl3): 8.36 (dd, J=15.2, 4.8 Hz, 2H), 7.46 (d, J=2.4 Hz, 1H), 6.97 (d, J=8.0 Hz, 1H), 7.26 (s, 1H), 6.67 (t, J=4.8 Hz, 1H), 6.39 (dd, J=8.0, 2.4, Hz, 1H), 2.20 (s, 3H); MS (ESI) m/e: 201 (M+H+).

Provenance & Evidence