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

HRID 1618925Notes

Reaction equation

HRID 1618925 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, 19.0 mmol, 1.0 equiv.) was dissolved in ethanol (50 ml), sparged under nitrogen, charged with 10% Pd/C (2.03 g, 1.90 mmol, 0.1 equiv.) and then sparged under hydrogen (1 atm). After stirring at room temperature for 5 hrs, the mixture was filtered through Celite and the residue was washed with MeOH. The filtrate was concentrated in vacuo to provide the titled compound. LRMS m/z (M+H) 205.0 found, 205.3 required.

Workup

  1. customsparged under nitrogen
  2. customsparged under hydrogen (1 atm)
  3. filtrationthe mixture was filtered through Celite
  4. washthe residue was washed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8f05079de14b4e29be64ae4cc9d44723
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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