Hydrochloric Acid → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

Participants

Reaction Steps

In a 1 l. 3-neck round bottom flask there was placed 30 g. of pivalyl acetonitrile, 13.5 g. of lithium hydroxide, 394 ml. of water and 281 ml. of ethanol. This mixture was heated to reflux and there was added thereto over a period of 10 minutes 94 ml. of an aqueous solution of 22.2 g. of hydroxylamine hydrochloride. The pH of the reaction mixture after the addition was complete was about 7.3. This pH was adjusted to about pH 6.7 using concentrated aqueous hydrochloric acid. After 30 minutes the pH was about 6.1. After 1 hour the pH was about 6.3. The pH was checked again at 2 hours and at 3 hours after the addition was complete and the pH at those times was about 6.6. A recheck of the pH at 4 hours, 5 hours, and 6 hours revealed the pH to be at about 6.7. The reaction mixture was then refluxed overnight. The following morning the pH was about 6.8. The reaction mixture was cooled and the ethanol removed from the mixture on the rotovapor at room temperature. A solid which separated was filtered off and dried. It weighed 18.65 g. and it was determined by vpc that the product contained 97% of the desired 3-amino-5-(t-butyl)isoxazole, and 1.6% of 5-amino-3-(t-butyl)isoxazole. Yield: 52% of desired isomer.

Provenance & Evidence