1-(2,2-Dimethylpropyl)-5-nitro-1H-1,2,3-benzotriazole → 1-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine

HRID 1626994Notes

Reaction equation

HRID 1626994 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[N:6]=[N:5]1>C(O)C.[Pd]>[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[N:6]=[N:5]1

Participants

4

Reactant 1

HCID 686564421-(2,2-Dimethylpropyl)-5-nitro-1H-1,2,3-benzotriazole

Product 1

HCID 686567951-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(2,2-Dimethylpropyl)-5-nitro-1H-1,2,3-benzotriazole (4.46 g, 19.04 mmol, 1.0 equiv.) was dissolved in ethanol (50 ml), flushed with nitrogen, and charged with 10% Pd/C (2.026 g, 1.904 mmol, 0.1 equiv.). After sparging with nitrogen, the mixture was sparged with hydrogen (1 atm) and stirred at ambient temperature for 5 hours. The mixture was filtered through Celite, the residue was washed with methanol and the filtrate was concentrated in vacuo, providing the titled compound. LRMS m/z (M+H) 205.0 found, 205.3 required.

Workup

  1. customflushed with nitrogen
  2. customAfter sparging with nitrogen
  3. customthe mixture was sparged with hydrogen (1 atm)
  4. filtrationThe mixture was filtered through Celite
  5. washthe residue was washed with methanol
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8fe48812b12c44fab0fcc40e26582bc2
Source dataset
uspto-grants-2014_07
Patent number
US08785482B2

Reaction notes

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