1-Methyl-4-[(4-nitrobenzyl)sulfonyl]benzene → 4-[[(4-Methylphenyl)sulfonyl]methyl]benzenamine

HRID 1277153

Reaction equation

HRID 1277153 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O>C(O)C.C(OCC)(=O)C.[Pd]>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([S:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:20][CH:19]=2)(=[O:11])=[O:10])=[CH:17][CH:16]=1

Participants

5

Reactant 1

HCID 8000821-Methyl-4-[(4-nitrobenzyl)sulfonyl]benzene

Product 1

HCID 15084184-[[(4-Methylphenyl)sulfonyl]methyl]benzenamineYield 89.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In ethanol (10 ml) and ethyl acetate (60 ml) was dissolved 4-methylphenyl 4-nitrobenzyl sulfone (0.5 g; G. Bram et al., Synthesis, 1987, 56-59). To the mixture was added 10% palladium on carbon (0.05 g) and catalytic hydrogenation was carried out at room temperature over night. The catalyst was filtered off, and the solvent was evaporated to give 4-aminobenzyl 4-methylphenyl sulfone (0.4 g) as colorless crystals.

Workup

  1. waitwas carried out at room temperature over night
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc288ac0ee8041d1891996a19d89cbbc
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Linked notes

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