Water → 2-Azidoaniline

HRID 859157Notes

Reaction equation

HRID 859157 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[N+:2]=[N-:3].NN.O>C(O)C>[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 234995172-Phthalimidophenyl azide

Product 1

HCID 108879562-AzidoanilineYield 25.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the of 2-(2-azido-phenyl)-isoindole-1,3-dione (373 mg, 1.4 mmol) in ethanol (10 mL) was added hydrazine (140 μL, 4.24 mmol) followed by stirring for 15 minutes. The reaction mixture was poured into water and was extracted with ethyl acetate (3×25 mL). The combined extracts were washed with water and brine and were dried over magnesium sulfate. Filtration and concentration in vacuo gave a residue which was purified via radial chromatography (1 mm plate, 10% ethyl acetate/hexanes to 33% ethyl acetate/hexanes gradient elution) to give 48 mg (25%) of 2-azidophenylamine as a solid: 1H NMR (300 MHz, DMSO-d6) δ 6.98 (m, 1H), 6.86 (m, 1H), 6.66–6.55 (m, 2H).

Workup

  1. extractionwas extracted with ethyl acetate (3×25 mL)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialwere dried over magnesium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customgave a residue which
  6. customwas purified via radial chromatography (1 mm plate, 10% ethyl acetate/hexanes to 33% ethyl acetate/hexanes gradient elution)

Sources & evidence

ORD record
ord-f79fd1d4e72e430588d8d183a9f20aca
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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