Ammonium Chloride → 2-Azidopyridin-4-amine

HRID 449911Notes

Reaction equation

HRID 449911 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[N-:9]=[N+:10]=[N-:11].[Na+].[NH4+].[Cl-]>CN(C=O)C>[N:9]([C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1)=[N+:10]=[N-:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 844322-Chloropyridin-4-amine

Product 1

HCID 189986302-Azidopyridin-4-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chloropyridin-4-amine (2.0 g, 15.6 mmol) in DMF (20 mL) under nitrogen was added NaN3 (2.0 g, 31.2 mmol) and NH4Cl (1.7 g, 31.2 mmol). The mixture was heated to 110° C. for 10 hours and then quenched with saturated Na2CO3. The reaction was filtered and then the filtrate was extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with water (50 mL), dried over Na2SO4, and concentrated under reduced pressure to afford 2-azidopyridin-4-amine (1.5 g, yield: 83%). LCMS (ESI) m/z: 136.2 [M+H+].

Workup

  1. customquenched with saturated Na2CO3
  2. filtrationThe reaction was filtered
  3. extractionthe filtrate was extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic extracts were washed with water (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b54e59707ff24fff94930663ba2d846a
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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