N-Methyl-2,6-dinitroaniline → N2-Methylbenzene-1,2,3-triamine

HRID 1665220

Reaction equation

HRID 1665220 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][C:4]=1[N+:12]([O-])=O>O1CCCC1.[Pd]>[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:12]

Participants

4

Reactant 1

HCID 80010N-Methyl-2,6-dinitroaniline

Product 1

HCID 12296380N2-Methylbenzene-1,2,3-triamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-methyl-2,6-dinitroaniline (407 mg, 2.06 mmol) in tetrahydrofuran (6.5 mL) was added palladium on carbon (45 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen for 5 hr at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound (280 mg, 2.04 mmol, 99%) as an oil.

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1ef500cda2824b619f923d67c0127569
Source dataset
uspto-grants-2011_10
Patent number
US08039500B2

Linked notes

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