Hydroxyamine hydrochloride → 5-p-Methoxybenzyloxy-1-hydroxy-2-hydroxymethyl-4-pyridone

Participants

Reaction Steps

To a solution of 39.3 g 5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone in 600 ml pyridine, was added 52.2 g hydroxylamine hydrochloride, and the mixture was heated at 70°-75° C. for 2.5 hours. The reaction mixture was concentrated to about 100 ml, 100 ml water was added to the concentrate, and the resulting solution was added under ice cooling to a mixture of 75 ml hydrochloric acid and 225 ml water. After adjusting the pH to 2-2.5, stirring was continued under ice cooling for 30 minutes, and the crystals which separated out were collected by filtration, washed with water and dried, giving 16.6 g of 5-p-methoxybenzyloxy-1-hydroxy-2-hydroxymethyl-4-pyridone.

Provenance & Evidence