3-Methoxy-2-nitroaniline → 3-Methoxybenzene-1,2-diamine

HRID 2409250Notes

Reaction equation

HRID 2409250 reaction equation
[N+:1]([C:4]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O>C(O)C.[Pd]>[CH3:12][O:11][C:10]1[C:4]([NH2:1])=[C:5]([NH2:6])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 104647003-Methoxy-2-nitroaniline

Product 1

HCID 1842683-Methoxybenzene-1,2-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-nitro-3-methoxyaniline (90 mg; 0.54 mmol) in ethanol (3 ml) was added 5% palladium on carbon (18 mg; 20 wt %). The resulting suspension was stirred at room temperature under an atmosphere of hydrogen for 18 hours. The suspension was then filtered through celite and the filtrate evaporated to give 3-methoxy-1,2-phenylenediamine (73 mg, 100%).

Workup

  1. filtrationThe suspension was then filtered through celite
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a9761a6d3d634b34aede28cc0d6abf3e
Source dataset
uspto-grants-2014_08
Patent number
US08815895B2

Reaction notes

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