Methyl iodide → 2-(N-Methyl-3-pyridinyl)-1-hydroxyethylidene bisphosphonic acid

HRID 275022Notes

Reaction equation

HRID 275022 reaction equation
[OH:1][C:2]([P:15](=[O:18])([OH:17])[OH:16])([P:11](=[O:14])([OH:13])[OH:12])[CH2:3][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.I[CH3:20]>[OH-].[Na+].O.C(O)C>[OH-:1].[OH:1][C:2]([P:15]([OH:16])([OH:17])=[O:18])([P:11]([OH:12])([OH:13])=[O:14])[CH2:3][CH2:4][C:5]1[CH:6]=[N+:7]([CH3:20])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 128523NE 58051

Product 1

HCID 1278732-(N-Methyl-3-pyridinyl)-1-hydroxyethylidene bisphosphonic acidYield 90.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

[1-Hydroxy-3-(3-pyridinyl)propylidene]bis[phosphonic acid](3.37 mmol 1.0 g) is dissolved in 8.4 ml of 1N NaOH solution with 29 ml of distilled water. Iodomethane (16.83 mmol, 1.05 ml) is added in 19 ml of ethanol. This reaction mixture is heated at 80° C. overnight. The solvent is evaporated in vacuo and the residue is triturated with acetone then recrystallized from ethanol and water to yield 0.5 g of 3-(3-hydroxy-3,3-diphosphonopropyl)-1-methyl pyridinium hydroxide, inner salt.

Workup

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is triturated with acetone
  3. customthen recrystallized from ethanol and water

Sources & evidence

ORD record
ord-15a4e3c7495d47779479767d3c586519
Source dataset
uspto-grants-1995_02
Patent number
US05391743

Reaction notes

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