4-Methoxy-2-nitroaniline → 4-Methoxy-o-phenylenediamine

HRID 2279396Notes

Reaction equation

HRID 2279396 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 1534044-Methoxy-o-phenylenediamineYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (1.0 g, 9.4 mmol, 0.15 eq) is added at room temperature to a stirred solution of 4-methoxy-2-nitro-phenylamine (10.0 g, 59.5 mmol, 1.0 eq) in methanol (70 mL). The mixture is hydrogenated for 72 hours, then filtered through decalite. Solvent is removed to afford 4-methoxy-benzene-1,2-diamine as a dark brown oil (8.0 g, 97% yield).

Workup

  1. filtrationfiltered through decalite
  2. customSolvent is removed

Sources & evidence

ORD record
ord-02c7153701c74ee7bbc553a65d5c6d6c
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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