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

HRID 872269Notes

Reaction equation

HRID 872269 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 (2-3) (4.46 g, 19.04 mmol, 1.0 equiv) was dissolved in ethanol (50 ml) and flushed with nitrogen, then charged with 10% Pd/C (2.026 g, 1.904 mmol, 0.1 equiv). The mixture was sparged under hydrogen (1 atm) and stirred at room temperature for 5 hrs. The mixture was filtered through a pad of Celite and the residue was washed with MeOH. The filtrate was concentrated to give the crude 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (2-4 LRMS m/z (M+H) 205.0 found, 205.3 required.

Workup

  1. customflushed with nitrogen
  2. customThe mixture was sparged under hydrogen (1 atm)
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washthe residue was washed with MeOH
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a0690a6c150a4bc1975887ba84c3546c
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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