Hydrochloric Acid → HCID 21074240, compound

Participants

Reaction Steps

Methyl 6-{[3-acetoxy-5-(2-methylbenzyloxy)benzoyl]amino}-3-pyridinecarboxylate (11.64 g, 26.8 mM) was dissolved in THF (150 ml) and sodium methoxide (25% in methanol) (11.6 ml, 53.6 mM) was added. The resulting yellow solution was stirred for 20 minutes at ambient temperature and was then added to dilute hydrochloric acid. The pH of the mixture was adjusted to pH=4 by the addition of sodium bicarbonate and acetic acid before ethyl acetate (50 ml) and water (25 ml) were added. This resulted in the precipitation of a colourless solid which was isolated by filtration and washed with water and ethyl acetate before being dried over magnesium sulphate, filtered, to give methyl 6-{[3-hydroxy-5-(2-methylbenzyloxy)benzoyl]amino}-3-pyridinecarboxylate as a colourless solid (9.62 g); H1 NMR δ (d6-DMSO) 2.33 (3H s) 3.85 (3H s) 5.11 (2H s) 6.61 (1H s) 7.01 (1H s) 7.18–7.29 (4H m) 7.40 (1H d) 8.32 (2H s) 8.90 (1H s) 9.77 (1H s) 11.04 (1H s).

Provenance & Evidence