4-Nitroaniline → 1-Azido-4-nitrobenzene

HRID 1892646Notes

Reaction equation

HRID 1892646 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-fb5b9a1d65674a018961a054d3e53894
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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