4-Nitroaniline → 1-Azido-4-nitrobenzene

HRID 1717227Notes

Reaction equation

HRID 1717227 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].N([O-])=O.[Na+].[N-:15]=[N+:16]=[N-].[Na+]>Cl>[N:8]([C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 1370491-Azido-4-nitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 4-nitroaniline (27.6 g) in 0.4N hydrochloric acid (500 ml) was added 1M aqueous sodium nitrite solution (200 ml) under ice-cooling, and the mixture was stirred for 30 min and then at room temperature for 20 min. An aqueous solution (100 ml) of sodium azide (13.0 g) was added to the obtained reaction mixture under ice-cooling, and the mixture was stirred for 30 min. The precipitated crystals were collected by filtration, washed with 1N hydrochloric acid and water and air-dried to give the title compound as a brown powder (28.2 g, 86%).

Workup

  1. temperaturecooling
  2. waitat room temperature for 20 min
  3. temperaturecooling
  4. stirringthe mixture was stirred for 30 min
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with 1N hydrochloric acid and water
  7. customair-dried

Sources & evidence

ORD record
ord-36b565f574de4015a8db62ba536a8c2f
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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