4-Chloropyridine → 4-Azidopyridine

HRID 2267143Notes

Reaction equation

HRID 2267143 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[N-:8]=[N+:9]=[N-:10].[Na+]>[OH-].[Na+].C(O)C.C(Cl)(Cl)Cl>[N:8]([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[N+:9]=[N-:10]

Participants

6

Reactant 2

HCID 122884-ChloropyridineHCID 33557Sodium Azide

Product 1

HCID 113324494-AzidopyridineYield 33.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

4-Chloropyridine (400 mg) was dissolved in 2.6 ml of a 1M aqueous solution of sodium hydroxide and 1.5 ml of ethanol, 340 mg of sodium azide was added to the solution at room temperature and the mixture was stirred at 110° C. for 4 hours. The reaction solution was returned to room temperature, diluted with chloroform and washed with water and then a saturated saline solution. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo to give 140 mg of the crude product of the title compound.

Workup

  1. additionwas added to the solution at room temperature
  2. customwas returned to room temperature
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-cec2debfa6384441a34adf336f79714e
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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