4-Nitroaniline → 1-Azido-4-nitrobenzene

HRID 537433Notes

Reaction equation

HRID 537433 reaction equation
N([O-])=O.[Na+].[N+:5]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)([O-:7])=[O:6].[N-:15]=[N+:16]=[N-].[Na+]>O.FC(F)(F)C(O)=O>[N:12]([C:11]1[CH:13]=[CH:14][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=1)=[N+:15]=[N-:16]

Participants

6

Reactant 3

HCID 74754-NitroanilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 1370491-Azido-4-nitrobenzeneYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of sodium nitrite (761 mg, 11 mmol) in water (5 mL) was added dropwise to a 0° C. solution of 4-nitroaniline (508 mg, 3.68 mmol) in trifluoroacetic acid (5 mL). After stirring for 10 minutes, a solution of sodium azide (1.55 g, 23.9 mmol) was added slowly. The resulting yellow suspension was stirred at room temperature for 5 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 1-azido-4-nitrobenzene (600 mg, 99%). 1H NMR (400 MHz, CDCl3, δ): 8.16-8.19 (m, 2H), 7.05-7.09 (m, 2H).

Workup

  1. stirringThe resulting yellow suspension was stirred at room temperature for 5 hours
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-ff08c3b6c4094b0a846b7c960e33125f
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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