Acetic Anhydride → 3-(N-formyl-N-hydroxyamino)-2-hydroxypropylphosphonic acid

HRID 1706220Notes

Reaction equation

HRID 1706220 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[OH:8][CH:9]([CH2:15][NH:16][OH:17])[CH2:10][P:11](=[O:14])([OH:13])[OH:12]>C(O)=O>[CH:1]([N:16]([CH2:15][CH:9]([OH:8])[CH2:10][P:11](=[O:13])([OH:12])[OH:14])[OH:17])=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 139616192-hydroxy-3-(N-hydroxyamino)propylphosphonic acid

Product 1

HCID 139616213-(N-formyl-N-hydroxyamino)-2-hydroxypropylphosphonic acidYield 16%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

Formic acid (300 mg.) was added dropwise to acetic anhydride (330 mg.) with stirring and the mixture was stirred for half an hour. To this solution were added 2-hydroxy-3-(N-hydroxyamino)propylphosphonic acid (430 mg.) and then formic acid (0.5 ml.), and the mixture was stirred for 1.5 hours at ambient temperature and then evaporated to dryness under reduced pressure. The oily residue was dissolved in methanol (10 ml.) and adjusted to pH 6-7 with conc. aqueous ammonium hydroxide solution to give oily precipitates which was collected by decantation and pulverized by triturating with methanol to give monoammonium salt of 3-(N-formyl-N-hydroxyamino)-2-hydroxypropylphosphonic acid (80 mg.).

Workup

  1. stirringthe mixture was stirred for half an hour
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe oily residue was dissolved in methanol (10 ml.)
  4. customto give oily
  5. customprecipitates which
  6. customwas collected by decantation
  7. customby triturating with methanol

Sources & evidence

ORD record
ord-4b8be6bd70084d9fb442a6d2e5644019
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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