Acetone → Incadronic acid

HRID 2248551Notes

Reaction equation

HRID 2248551 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-de6805587d514dc9898b707b9071c0c6
Source dataset
uspto-grants-1991_08
Patent number
US05041428

Reaction notes

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