(4-Nitrophenyl)methanesulfonamide → 1-(4-Aminophenyl)methanesulfonamide

HRID 1194765Notes

Reaction equation

HRID 1194765 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([NH2:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([NH2:14])(=[O:12])=[O:13])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 2755281(4-Nitrophenyl)methanesulfonamide

Product 1

HCID 108214071-(4-Aminophenyl)methanesulfonamideYield 77.1%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-nitrobenzenemethanesulphonamide (7.11 g) and 5% palladium oxide on charcoal (1.4 g) in ethanol (1.1 l) was hydrogenated at room temperature and pressure. The reaction was terminated after 2.5 l of hydrogen had been absorbed and the catalyst was removed by filtration. The filtrate was concentrated to give the title compoun as a solid (4.72 g). Recrystallisation of a sample from ethanol gave analytically pure material m.p. 166° (bubbles).

Workup

  1. customwas hydrogenated at room temperature
  2. customThe reaction was terminated after 2.5 l of hydrogen
  3. customhad been absorbed
  4. customthe catalyst was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bd06854f2cb345d283bd61fd4005378e
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

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