Sodium Iodide → HCID 86708938, compound

HRID 1500003Notes

Reaction equation

HRID 1500003 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[NH2:10][C:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=1.[Na+].[I-]>CC(C)=O>[Cl-:1].[NH2:10][C:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N+:12]=1[CH2:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 281142-Amino-3-HydroxypyridineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 86708938HCID 86708938, compoundYield 194.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2-chloro-5-chloromethyl-pyridine (1.0 g, 6.17 mmol), 2-amino-pyridin-3-ol (0.68 g, 6.17 mmol) and NaI (0.93 g, 6.17 mmol) in acetone (10 mL) was refluxed for 12 h. After cooling to room temperature, solids were removed by filtration and the filtrate was evaporated under reduced pressure. The residue was triturated with ethyl acetate to yield 1.63 g of crude 2-amino-1-(6-chloro-pyridin-3-ylmethyl)-3-hydroxy-pyridinium chloride wich was used without further purification.

Workup

  1. temperaturewas refluxed for 12 h
  2. customsolids were removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-e77fdc1d28c1453884fc85ebb1da6402
Source dataset
uspto-grants-2015_12
Patent number
US09204651B2

Reaction notes

Loading…