Acetic Acid → 3-(Hydroxyamino)propylphosphonic acid

A mixture of diethyl 3-(N-benzyloxy-N-tosylamino)propylphosphonate (13.2 g), conc. hydrochloric acid (130 ml) and acetic acid (130 ml) was refluxed with stirring for 45 hours. The resultant mixture was concentrated under reduced pressure to give a residue and then water and an activated charcoal was added thereto, whereafter the mixture was filtered. The filtrate was concentrated under reduced pressure, and the resultant residual oil (8.59 g) was dissolved in water (25 ml). To the solution were added pyridine (2.08 g) and ethanol (5 ml), and then the mixture was allowed to stand overnight at 4° C. to give 3-(N-hydroxyamino)propylphosphonic acid (2.30 g) in the form of crystals. MP: 160°-166° C. (dec.).

1. temperaturewas refluxed
2. concentrationThe resultant mixture was concentrated under reduced pressure
3. customto give a residue
4. filtrationwhereafter the mixture was filtered
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionthe resultant residual oil (8.59 g) was dissolved in water (25 ml)
7. additionTo the solution were added pyridine (2.08 g) and ethanol (5 ml)
8. waitto stand overnight at 4° C.

ORD record

ord-7ebae7d6fe9a4b51b45084ab10a6e6cf

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04206156