Acetic Acid → 3-(Hydroxyamino)propylphosphonic acid

A mixture of diethyl 3-(N-hydroxyamino)propylphosphonate (12.9 g.), acetic acid (65 ml.) and 1 N hydrochloric acid (130 ml.) was heated to reflux with stirring for 8 hours and then was concentrated under reduced pressure to remove off acetic acid. The concentrate was decolorized by treating with an activated charcoal and evaporated to dryness under reduced pressure to give an oily residue (9.5 g.), which was dissolved in water (30 ml.) and adjusted to pH 4 with sodium bicarbonate (ca. 4.2 g.) to give crystals of 3-(N-hydroxyamino)propylphosphonic acid (4.80 g.), m.p. 160°-163.5° C. (decomp.). An additional crystals of the same object compound (0.91 g.) was recovered from the mother liquor after standing overnight at ambient temperature (m.p. 159°-163° C. (decomp.)). The I.R. and N.M.R. spectra of these crystals were superimposable with those of the authentic specimen (m.p. 160°-166° C. (decomp.)).

1. temperaturewas heated
2. temperatureto reflux
3. concentrationwas concentrated under reduced pressure
4. customto remove off acetic acid
5. additionby treating with an activated charcoal
6. customevaporated to dryness under reduced pressure
7. customto give an oily residue (9.5 g.), which

ORD record

ord-68ec09664efb4cb2a7acaf214c4f5cb1

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04182758