Acetone → Incadronic acid

HRID 1073687Notes

Reaction equation

HRID 1073687 reaction equation
[CH:1]1([NH:8][CH:9]([P:18](=[O:25])([O:22]CC)[O:19]CC)[P:10](=[O:17])([O:14]CC)[O:11]CC)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.CC(C)=O>Cl>[CH:1]1([NH:8][CH:9]([P:18](=[O:19])([OH:22])[OH:25])[P:10](=[O:11])([OH:14])[OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 5325128HCID 5325128, compound

Product 1

HCID 3699Incadronic acidYield 86.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4.0 g of tetraethyl (cycloheptylamino)methylenebis(phosphonate) was dissolved in 40 ml of concentrated hydrochloric acid and heated under reflux for 2.5 hours. After cooling, the reaction solution was concentrated under reduced pressure to eliminate hydrochloric acid. Then, 30 ml of purified water was added to the residue and the mixture was again concentrated under reduced pressure. The oily product thus obtained was solidified by methanol and acetone and subject to the filtration. The residue was washed with acetone to give 2.5 g of (cycloheptylamino)methylenebis(phosphonic acid) as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. additionThen, 30 ml of purified water was added to the residue
  6. concentrationthe mixture was again concentrated under reduced pressure
  7. customThe oily product thus obtained
  8. filtrationsubject to the filtration
  9. washThe residue was washed with acetone

Sources & evidence

ORD record
ord-a0bb455225db41c0bce1cb367feb6f38
Source dataset
uspto-grants-1990_11
Patent number
US04970335

Reaction notes

Loading…