3-Nitro-N-(acetyl)benzenesulfonamide → N-(3-aminophenyl)sulfonylacetamide

HRID 2379327Notes

Reaction equation

HRID 2379327 reaction equation
[CH3:1][C:2]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)(=[O:7])=[O:6])=[O:3]>[Pd].O.C(O)C>[CH3:1][C:2]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)(=[O:7])=[O:6])=[O:3]

Participants

5

Reactant 1

HCID 189578003-Nitro-N-(acetyl)benzenesulfonamide

Product 1

HCID 504048N-(3-aminophenyl)sulfonylacetamideYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 1-(methylcarbonylaminosulphonyl)-3-nitrobenzene (2.9 g, 12 mmol), 10% palladium on carbon (0.4 g, 14% (w/w)) in water (3 ml) and ethanol (150 ml), the title compound (1.8 g, 70%) was afforded as a colourless soiid. mp 148°-150° C. 1H NMR (360 MHz, D6 -DMSO) δ 1.92 (3H, s), 5.64 (2H, brs), 6.80 (1H, dd, J=8.0 and 1.7 Hz), 6.98 (1H, d, J=7.6 Hz), 7.10 (1H, dd, J=2.0 and 2.0 Hz), 7.21 (1H, dd, J=7.9 and 7.9 Hz), 11.87 (1H, brs).

Sources & evidence

ORD record
ord-7f8533e15def43c2a3596b448a96a197
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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