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 82.30 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-a0c314ce0a394e4e98d5f041228f51b7

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04182758