2-Methoxy-1,3-dimethyl-5-nitrobenzene → 4-Methoxy-3,5-dimethylaniline

HRID 1488450Notes

Reaction equation

HRID 1488450 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[O:12][CH3:13]>[Pd].C(O)C>[NH2:8][C:6]1[CH:5]=[C:4]([CH3:11])[C:3]([O:12][CH3:13])=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 1398352-Methoxy-1,3-dimethyl-5-nitrobenzene

Product 1

HCID 41660974-Methoxy-3,5-dimethylanilineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,6-Dimethyl-4-nitroanisole (3, 29 g, 160 mmol), 10% Pd-C (200 mg) and ethanol (300 mL) were placed in a 500-mL Parr hydrogenation flask and hydrogenated at 50 psi for 24 h. The resulting solution was filtered through a silica gel column using ethyl acetate as eluent. Concentration of the solvent and drying under vacuum gave 23.7 g (98% yield) of 4-amino-2,6-dimethylanisole (4) as a brown-colored solid, mp 59°-60° C. (lit.: Bruice, T. C.; Kharasch, N.; Winzler, R. J. J. Org. Chem. 1953, 18, 83; 63° C.).

Workup

  1. filtrationThe resulting solution was filtered through a silica gel column
  2. customConcentration of the solvent and drying under vacuum

Sources & evidence

ORD record
ord-2ddd5943ec0b486c9b2d73d88245614b
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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