1-(Methanesulfonylmethyl)-4-nitrobenzene → 4-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)

HRID 359455Notes

Reaction equation

HRID 359455 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 2873701-(Methanesulfonylmethyl)-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 128439644-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)Yield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-[(methylsulphonyl)methyl]-4-nitrobenzene (4 g) in ethyl acetate (300 ml) containing a catalytic amount of palladium on carbon (10%, prehydrogenated, 0.5 g) was hydrogenated at room temperature and pressure until hydrogen uptake ceased (1400 ml, 1 h). The catalyst was filtered off and the filter cake washed with warm ethanol (2×80 ml). The filtrates were combined and concentrated under vacuum to afford the title compound (1.9 g) as a pale yellow crystalline solid, m.p. 167°-168° C.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(1400 ml, 1 h)
  3. filtrationThe catalyst was filtered off
  4. washthe filter cake washed with warm ethanol (2×80 ml)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f8bc6ecea16644b99610ca9b3f5cb226
Source dataset
uspto-grants-1991_03
Patent number
US05001135

Reaction notes

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