N-(3-methoxy-5-nitrophenyl)methanesulfonamide → N-(3-amino-5-methoxyphenyl)methanesulfonamide

HRID 1052639Notes

Reaction equation

HRID 1052639 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1>C(O)(=O)C.[Fe]>[NH2:9][C:7]1[CH:6]=[C:5]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 68836539N-(3-methoxy-5-nitrophenyl)methanesulfonamide

Product 1

HCID 68840230N-(3-amino-5-methoxyphenyl)methanesulfonamideYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

N-(3-Methoxy-5-nitrophenyl)methanesulfonamide (3 g, 11.82 mmol) was treated with iron powder (3.3 g, 59.09 mmol) in acetic acid (120 ml) and stirred at 40° C. for 2 h. The crude was then filtered over Celite and the solvent was removed in vacuum. A mixture of a solution of sodium bicarbonate 4% and ethyl acetate was added and the resulting mixture was filtered over Celite. The organic phase was washed with water and brine, dried over magnesium sulphate and the solvent was remove to give 2.53 g (86% yield) of the title compound as a dark solid, that was used in the next step without further purification. Purity 87%.

Workup

  1. filtrationThe crude was then filtered over Celite
  2. customthe solvent was removed in vacuum
  3. additionA mixture of a solution of sodium bicarbonate 4% and ethyl acetate
  4. additionwas added
  5. filtrationthe resulting mixture was filtered over Celite
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent was remove

Sources & evidence

ORD record
ord-78a0fc98293c40718cba05cd5a33f48c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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