Hydrochloric Acid → HCID 178439659, compound

Participants

Reaction Steps

A mixture of 1.00 g (2.65 mmoles) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-cyano-4H-pyrido[1,2-a]-pyrimidin-4-one, 0.97 g (7.27 mmoles) of aluminum chloride, 1.43 g (21.99 mmoles) of sodium azide and 20 ml of tetrahydrofuran was heated under reflux for 2 hours. After cooling, the resulting reaction solution was diluted with ice water and then acidified with dilute hydrochloric acid. The precipitate so formed was collected by filtration and dried. 1.09 g (2.59 mmoles) of this precipitate was suspended in 55 ml of menthanol and then dissolved therein by adding 3.00 ml (2.55 mmoles) of a 5.6% ethanolic solution of potassium hydroxide. The resulting solution was filtered to remove any insoluble matter, and the filtrate was cooled. The precipitate which separated out was collected by filtration to obtain 0.88 g (74% yield) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-(1H- tetrazol-5-yl)-4H-pyrido[ 1,2-a]pyrimidin-4-one potassium salt. Subsequently, 0.88 g (1.92 mmoles) of this potassium salt was dissolved in 180 ml of water by warming and the resulting solution was neutralized with 1.23 ml (3.69 mmoles) of 3N hydrochloric acid. The precipitate so formed was collected by filtration to obtain 0.78 g (97% yield) of 9-[(4-acetyl-3- hydroxy-2-n-propylphenoxy)methyl]-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one in the form of a white powder. This powder had a melting point of 268°-271° C. (dec.) and its infrared absorption spectrum and elemental analysis were as follows:

Provenance & Evidence