1-(Methylsulphonylaminocarbonyl)-3-nitrobenzene → 1-(Methylsulphonylaminocarbonyl)-3-aminobenzene

HRID 2399684Notes

Reaction equation

HRID 2399684 reaction equation
[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:7])(=[O:4])=[O:3]>C(O)C.[Pd].O>[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)=[O:7])(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

Product 1

HCID 212017011-(Methylsulphonylaminocarbonyl)-3-aminobenzeneYield 84.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-(methylsulphonylaminocarbonyl)-3-nitrobenzene (4 g, 16 mmol) in ethanol (100 ml) was added 10% palladium on carbon (0.5 g, 12.5% (w/w)) in water (5 ml). The mixture was hydrogenated at 40 psi for 10 min then the catalyst was filtered off and washed with ethanol. The solvent was evaporated in vacuo to give the title compound (2.9 g, 83%) as a tan powder after trituration with diethyl ether, mp 153°-155° C. 1H NMR (360 MHz, D6 -DMSO) δ 3.3 (3H, s), 6.79 (1H, d, J=7.7 Hz), 7.05 (1H, d, J=7.7 Hz), 7.08 (1H, d, J=1.9 Hz), 7.13 (1H, dd, J=7.7 and 7.7 Hz).

Workup

  1. filtrationthe catalyst was filtered off
  2. washwashed with ethanol
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bd34a347789b4f7194dd75e497f74334
Source dataset
uspto-grants-1995_09
Patent number
US05451582

Reaction notes

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