Citric Acid → HCID 21109706, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-6-chloro-nicotinic acid methyl ester (1 g) and N-(2-methoxyethyl)methylamine (0.89 g) in 1,8-diazabicyclo[5.4.0]undec-7-ene (1.519 g) was stirred at 60° C. for 3 h and at 90° C. for 1 h. 2 M NaOH (3.99 ml) was added and the mixture was stirred at 90° C. for 15 min. After cooling to room temperature 2 M HCl (3.99 ml) was added. The mixture was acidified using concentrated citric acid solution. The mixture was extracted with ethyl acetate. The org. phase was washed with brine, dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2/MeOH 4:1) to give 5-bromo-6-[(2-methoxy-ethyl)-methyl-amino]-nicotinic acid (1.06 g) as a white solid.

Provenance & Evidence