Sodium Hydroxide → HCID 86659956, compound

HRID 2366073Notes

Reaction equation

HRID 2366073 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.Br.Br[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 178516507HCID 178516507, compound

Product 1

HCID 86659956HCID 86659956, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2 g (15.4 mmol) of 2-chloropyridin-4-ol, 3.82 g (15.1 mmol) of 3-(bromomethyl)pyridine hydrobromide, 3 g (75.6 mmol) of sodium hydroxide and 1.39 g (4.3 mmol) of tetrabutylammonium bromide in 90 mL of toluene is refluxed for 12 hours. After cooling to room temperature, the reaction medium is taken up in 300 mL of EtOAc, washed successively with water (2×100 mL), with saturated NaHCO3 solution (100 mL) and with brine (100 mL), dried over Na2SO4, filtered, concentrated under reduced pressure and then purified by chromatography on silica gel, eluting with a 98/2 DCM/MeOH mixture. 2.5 g of 2-chloro-4-(pyridin-3-ylmethoxy)pyridine are obtained in the form of a yellow oil.

Workup

  1. temperatureis refluxed for 12 hours
  2. washwashed successively with water (2×100 mL), with saturated NaHCO3 solution (100 mL) and with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography on silica gel
  7. washeluting with a 98/2 DCM/MeOH mixture

Sources & evidence

ORD record
ord-5e9b8b64325943bbb91386e2650e481c
Source dataset
uspto-grants-2014_04
Patent number
US08697731B2

Reaction notes

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