Ammonium Chloride → 2-Azidopyridin-4-amine

HRID 2260572Notes

Reaction equation

HRID 2260572 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[NH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10](Cl)[CH:9]=1>CN(C)C=O>[NH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([N:1]=[N+:2]=[N-:3])[CH:9]=1

Participants

5

Reactant 3

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

Product 1

HCID 189986302-Azidopyridin-4-amineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Sodium azide (1.31 g) and ammonium chloride (1.07 g) were added to a solution of 4-amino-2-chloropyridine (2 g) in dimethylformamide (20 ml) and the mixture was stirred at 110° C. for 10 hours. After the insoluble material was filtered off, the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to give 1.83 g of 4-amino-2-azidopyridine, melting point 220° C. (decomposition).

Workup

  1. filtrationAfter the insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dac22f78105f4a9ab0f12768bb2b7f42
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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