Potassium Hydroxide → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

In a 100 ml. round bottom 3-neck flask there was placed 2 g. of pivalyl acetonitrile, 0.9 g. of potassium hydroxide, 25 ml. of ethanol, and 35 ml. of water. The mixture was heated to refluxing, and an aqueous solution of hydroxylamine hydrochloride was added. After the addition was complete, the mixture showed a pH of 5.6. The pH was immediately adjusted to 6.2 by adding aqueous saturated sodium bicarbonate solution. The pH of the reaction mixture after 1 hour was 6.3. After 2 hours, the pH of the reaction mixture was 6.4. After 3 hours, the pH of the reaction mixture was 6.5. The reaction mixture was allowed to reflux overnight, and the following morning the pH was 6.8. The reaction mixture was cooled and the ethanol stripped on the rotovapor. The white solid which separated was filtered off and dried. The solid weighed 0.8 g., and was determined by vpc to contain 91.9% 3-amino-5-(t-butyl)isoxazole and 5.7% of 5-amino-3-(t-butyl)isoxazole. Yield of desired isomer was 48%.

1. customround bottom 3-neck flask there was placed
2. temperatureThe mixture was heated
3. temperatureto refluxing
4. additionAfter the addition
5. waitAfter 2 hours
6. waitAfter 3 hours
7. temperatureto reflux overnight
8. temperatureThe reaction mixture was cooled
9. customThe white solid which separated
10. filtrationwas filtered off
11. customdried

ORD record

ord-675672c343db4e66a62a4067c414496d

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04259501