1-(3-Nitrophenyl)-1H-1,2,3-triazole → 3-(1H-1,2,3-triazol-1-yl)benzenamine

HRID 2244464Notes

Reaction equation

HRID 2244464 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[CH:13][N:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO.C1COCC1.[Pd]>[N:10]1([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)[CH:14]=[CH:13][N:12]=[N:11]1

Participants

6

Reactant 2

HCID 441562971-(3-Nitrophenyl)-1H-1,2,3-triazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 591998983-(1H-1,2,3-triazol-1-yl)benzenamineYield 101.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Nitro-phenyl)-1H-[1,2,3]triazole (9.66 g, 51 mmol) were dissolved in 300 ml methanol and 70 ml THF. Palladium on charcoal (10%, 500 mg) were added and the reaction mixture was stirred with a hydrogen balloon for 36 h. Palladium on charcoal was filtered off and washed with methanol. The solvent was evaporated off to yield the title compound (8.3 g, 100%) as an off-white solid, mp 71-73° C.

Workup

  1. filtrationPalladium on charcoal was filtered off
  2. washwashed with methanol
  3. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-4d09d7af4e02434aaeb55865083a3e4d
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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