Sodium hydride → HCID 14116888, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (420 mg of 0%, 10.5 mmoles) in DMF (10 ml) was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (1.612 g, mmoles) and the mixture stirred for 20 minutes, followed by cooling (ice water) and addition of methyl bromoacetate (832 mg, 5.44 mmoles). The mixture was stirred for 20 minutes in the cold and another 10 minutes at ambient temperature followed by pouring into 70 ml of ice-cold water. A separated solid was filtered and dried to give 1.58 g of crude product mp 92°-94°. This was recrystallized from methylene chloride-ether to give 1.21 g of the title compound as a white crystalline solid, mp 94°-95° (67.6% yield). The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ8.2 (s, 1H); 6.16 (s, 1H); 4.7 (s, 2H); 4.40 (bs, H); 3.86 (s, 3H); 3.54 (m, 2H); 2.6 (m, 6H); 1.04 (t, 6H).

Provenance & Evidence