Ethyl bromoacetate → HCID 59596525, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (9.0 g, 60% dispersion, 225 mmol) was suspended in DMF (150 mL) and cooled to 0-5° C. A solution of 4-methylamino-nicotinonitrile (20.0 g, 150 mmol) in DMF (100 mL) was added dropwise over ca. 20 minutes and the resulting mixture stirred cold for 30 minutes and then treated with a solution of ethyl bromoacetate (34.0 g, 225 mmol) in DMF (50 mL). The solution was allowed to warm to room temperature over 1 hour. The mixture was partitioned between ethyl acetate and water and the aqueous further extracted with ethyl acetate. The combined organic layers were washed with water (×2), brine, dried (MgSO4) and evaporated. Trituration of the resultant residue with ethyl acetate gave the title compound (12.2 g, 37%) as a yellow solid. 1H NMR (CDCl3) 1.44 (3H, t, J=7.1 Hz), 3.88 (3H, s), 4.43 (2H, q, J=7.1 Hz), 5.09 (2H, br s), 7.10 (1H, dd, 1H, J=6.1, 1.0 Hz), 8.35 (1H, d, J=6.1 Hz), 8.88 (1H, d, J=1.0 Hz).

Provenance & Evidence