3-Aminopyridine → 3-Azidopyridine

HRID 2267126Notes

Reaction equation

HRID 2267126 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].N[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.N([O-])=O.[Na+]>O.Cl.C(Cl)(Cl)Cl>[N:1]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 3

HCID 100093-AminopyridineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 120666873-AzidopyridineYield 97.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

Sodium azide (1.5 g) dissolved in 5 ml of water was dropped into a solution of 2.0 g of 3-aminopyridine in 15 ml of 10% hydrochloric acid under cooling with ice. After the reaction solution was stirred for 20 minutes under cooling with ice, 1.8 g of sodium nitrite dissolved in 5 ml of water was dropped in the reaction solution. After temperature of the reaction solution was raised up to room temperature, it was stirred for 1 hour. The reaction solution was diluted with chloroform, washed with water and then with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 2.5 g of the title crude compound as a brown oily substance.

Workup

  1. temperatureunder cooling with ice
  2. additionwas dropped in the reaction solution
  3. stirringwas stirred for 1 hour
  4. washwashed with water
  5. dry with materialwith a saturated saline solution and dried over sodium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-447a2c1e9f7b45559dadfa0cff6773d9
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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