Hydroxyamine hydrochloride → HCID 136408874, compound

To a mixture of 0.176 g. of p-nitrobenzyl p-hydroxyphenylglyoxylate and 1 g. of hydroxylamine hydrochloride were added 9 ml. of N,O-bis-trimethylsilyltrifluoroacetamide and the solution was stirred at a temperature of 140° C. for 2 hours. The reaction mixture was evaporated under reduced pressure and the residue was taken up in ethyl acetate. The ethyl acetate solution was washed with water and was then dried and evaporated. The oxime product was purified and isolated over silica gel preparative plates using toluene:ethyl acetate, 7:3, for elution. The product was located on the plate by means of UV light and the silica gel was scraped from the plate and the product extracted therefrom with ethyl acetate. The ethyl acetate was evaporated to yield 186 mg. of product. The product was crystallized from methylene chloride to yield 103 mg. of the crystalline material. The filtrate from the crystallization was diluted with petroleum ether to yield a second crop of 20 mg.

1. additionTo a mixture of 0.176 g
2. customThe reaction mixture was evaporated under reduced pressure
3. washThe ethyl acetate solution was washed with water
4. customwas then dried
5. customevaporated
6. customThe oxime product was purified
7. customisolated over silica gel preparative plates
8. washethyl acetate, 7:3, for elution
9. extractionthe product extracted
10. customThe ethyl acetate was evaporated
11. customto yield 186 mg
12. customThe product was crystallized from methylene chloride
13. customto yield 103 mg
14. customThe filtrate from the crystallization
15. additionwas diluted with petroleum ether
16. customto yield a second crop of 20 mg

ORD record

ord-824b2805bb7f49b396d3e0c3532ae24c

Source dataset

uspto-grants-1982_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04355172