3-nitro-N-(phenylsulfonyl)Benzamide → 3-Amino-N-(phenylsulfonyl)benzamide

HRID 2379326Notes

Reaction equation

HRID 2379326 reaction equation
[C:1]1([S:7]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].O.C(O)C>[C:1]1([S:7]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[O:12])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 9757333-nitro-N-(phenylsulfonyl)Benzamide

Product 1

HCID 184055003-Amino-N-(phenylsulfonyl)benzamideYield 67.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 1-(phenylsulphonylaminocarbonyl)-3-nitrobenzene (5 g, 16 mmol), 10% palladium on carbon (0.5 g, 10% (w/w)) in water (3 ml) and ethanol (100 ml), the title compound (3 g,67%) was afforded as a pale beige solid after recrystallisation from ethanol. mp 135°-138° C. 1H NMR (360 MHz, D6 -DMSO) δ 6.75-6.78 (1H, m), 6.96-6.98 (2H, m), 7.10 (1H, dd, J=8.0 and 8.0 Hz), 7.60-7.73 (3H, m), 7.97 (2H, m).

Sources & evidence

ORD record
ord-8768efc08474453587935b8e1019de6f
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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