Sodium Hydroxide → 4-(3-bromo-1H-1,2,4-triazol-1-yl)aniline

HRID 40731Notes

Reaction equation

HRID 40731 reaction equation
[Br:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[N:3]=1.[OH-].[Na+]>CCO>[Br:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 446274753-Bromo-1-(4-nitrophenyl)-1H-1,2,4-triazole

Product 1

HCID 446274774-(3-bromo-1H-1,2,4-triazol-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-1-(4-nitrophenyl)-1H-1,2,4-triazole (0.51 g, 1.9 mmol), SnCl2-2H2O (2.14 g, 9.5 mmol) and EtOH (4 mL) was heated at reflux for 4 h. The reaction mixture was cooled to room temperature and basified with NaOH (2M aq.) until pH 7˜9. The resulting precipitate was filtered through Celite and washed with EtOH. The EtOH filtrate was concentrated in vacuo and the crude residue was dissolved in water and extracted with EtOAc (3×). The combined organics were dried (MgSO4) and concentrated in vacuo to provide the desired product as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.28 (s, 1H), 7.40 (d, 2H), 6.79 (d, 2H), 3.90 (br s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. filtrationThe resulting precipitate was filtered through Celite
  4. washwashed with EtOH
  5. concentrationThe EtOH filtrate was concentrated in vacuo
  6. dissolutionthe crude residue was dissolved in water
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organics were dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-877f50c364bd4c8c83032d3c977b9e72
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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