Ammonium Chloride → 5-Amino-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 2374148Notes

Reaction equation

HRID 2374148 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-])=O.[Cl-].[NH4+].[In]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 63812334HCID 63812334, compound

Product 1

HCID 583815765-Amino-2-(1H-1,2,4-triazol-1-yl)benzonitrileYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Nitro-2-[1,2,4]triazol-1-yl-benzonitrile (1.14 g, 5.3 mmol) was dissolved in ethanol (23 mL) and satd. aq. ammonium chloride (5.3 mL) before adding indium powder (3.25 g, 28.2 mmol). The mixture was then refluxed for 3 h, cooled to RT, and the solids filtered (MeOH washed). The filtrate was diluted with water, basified with 1N NaOH (aq), and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated under vacuum to yield the title compound (0.88 g). MS (ESI+) for m/z 186 (M+H)+.

Workup

  1. temperatureThe mixture was then refluxed for 3 h
  2. filtrationthe solids filtered
  3. wash(MeOH washed)
  4. additionThe filtrate was diluted with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-951b5b557a5a4b68ac799f381aa626f1
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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