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

HRID 2281054Notes

Reaction equation

HRID 2281054 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), sparged under an atmosphere of nitrogen and charged with 10% Pd/C (2.026 g, 1.904 mmol, 0.1 equiv.). The mixture was sparged under an atmosphere of hydrogen (1 atm) and stirred vigorously at ambient temperature for 5 hours. The mixture was filtered through Celite and the residue was washed with methanol. The filtrate was concentrated in vacuo, providing the titled compound. LRMS m/z (M+H) 205.0 found, 205.3 required.

Workup

  1. customsparged under an atmosphere of nitrogen
  2. customThe mixture was sparged under an atmosphere of hydrogen (1 atm)
  3. filtrationThe mixture was filtered through Celite
  4. washthe residue was washed with methanol
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f10bf80758bc4fde8e3248f68005b57a
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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