Nitrogen → HCID 67888635, compound

HRID 1626958Notes

Reaction equation

HRID 1626958 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[N+:13]([O-])=O.N#N>C(O)C.[Pd]>[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][NH:4][C:5]1[C:6]([NH2:13])=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 61166465HCID 61166465, compound

Product 1

HCID 67888635HCID 67888635, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2,2-Dimethylpropyl)-4-methoxy-2-nitroaniline (3) (15.3 g, 64.2 mmol, 1.0 equiv.) was dissolved in ethanol (200 ml). After purging the reaction mixture with N2, 10% palladium on carbon (13.67 g, 12.84 mmol, 0.2 equiv.) was added. The mixture was sparged under an atmosphere of hydrogen (1 atm) at room temperature. When LCMS showed completion of the hydrogenation, the mixture was filtered through Celite filter. The Pd/C residue was washed thoroughly with MeOH. The filtrate was then concentrated in vacuo to give N1-(2,2-dimethylpropyl)-4-methoxybenzene-1,2-diamine (4) as a dark red oil. LRMS m/z (M+H) 209.0 found, 209.2 required.

Workup

  1. additionwas added
  2. customThe mixture was sparged under an atmosphere of hydrogen (1 atm) at room temperature
  3. filtrationthe mixture was filtered through Celite
  4. filtrationfilter
  5. washThe Pd/C residue was washed thoroughly with MeOH
  6. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-2fc86d094184433abf5c631da998b9e1
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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