N-(3-Amino-4-chlorophenyl)-2,2-dimethylpropanamide synthesis

Yield:30758-15-7 69%

Reaction Conditions:

with pyridine at 20; for 60 h;

Steps:

132.a

Pivaloyl chloride (2.71 mL, 22.0 mmol) was injected dropwise into a stirred solution of 4-chloro-1 ,3-benzenediamine (2.85 g, 20.0 mmol) in pyridine (20 mL) at room temperature. After stirring 60 h, water (200 mL) was added and the mixture extracted with ethyl acetate. The extracts were washed with 0.1 M aqueous hydrochloric acid, water and brine, dried (MgSO₄) and evaporated under reduced pressure. The residue was recrystallised (toluene) to give the title compound (3.11 g, 69%) as a solid. 1 H NMR (400MHz, DMSO-d₆) δ 1.20 (s, 9H),5.26 (s, 2H), 6.77 (dd, J = 8.6, 2.5 Hz, 1 H), 7.06 (d, J = 8.6 Hz, 1 H), 7.22 (d, J = 2.5 Hz, 1H), 9.01 (s, 1H).

References:

WO2006/127458,2006,A2 Location in patent:Page/Page column 109