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-b46d7fffdd664a1882f8d97922641142

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04206156