1-(Methanesulfonyl)-3-methoxy-5-nitrobenzene → 3-Methanesulfonyl-5-methoxyaniline

HRID 1957966Notes

Reaction equation

HRID 1957966 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([O:14][CH3:15])[CH:6]=1)(=[O:4])=[O:3]>CO.ClCCl.[Pd]>[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([O:14][CH3:15])[CH:6]=1)[NH2:11])(=[O:3])=[O:4]

Participants

5

Reactant 1

HCID 578630801-(Methanesulfonyl)-3-methoxy-5-nitrobenzene

Product 1

HCID 578631053-Methanesulfonyl-5-methoxyaniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-Methylsulfonyl-3-methoxy-5-nitro-benzene (1.3 g; 5.6 mmol) was dissolved in methanol (40 ml) and 80 mg Pd/C (5% w/w) were added and the reaction mixture was hydrogenated at 2 bar. The mixture was then diluted with dichloromethane, filtrated above over a celite pad, concentrated and the residual was crystallized from methanol. 0.5 g (2.48 mmol; 44% yield) of a solid were obtained.

Workup

  1. filtrationfiltrated above over a celite pad
  2. concentrationconcentrated
  3. customthe residual was crystallized from methanol
  4. custom0.5 g (2.48 mmol; 44% yield) of a solid were obtained

Sources & evidence

ORD record
ord-b452befcd1ed49aab7fdd283b760b9ea
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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