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

HRID 2379339Notes

Reaction equation

HRID 2379339 reaction equation
[CH2:1]([S:3]([NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)=[O:8])(=[O:5])=[O:4])[CH3:2]>[Pd].O.C(O)C>[CH2:1]([S:3]([NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)=[O:8])(=[O:4])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 189577921-(Ethylsulphonylaminocarbonyl)-3-nitrobenzene

Product 1

HCID 189577811-(Ethylsulphonylaminocarbonyl)-3-aminobenzeneYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 1-(ethylsulphonylaminocarbonyl )-3-nitrobenzene (3 g, 11.6 mmol), 10% palladium on carbon (0.3 g, 10% (w/w)) in water (3 ml) and ethanol (100 ml), the title compound (1.95 g, 74%) was afforded as a pale beige solid after recrystallisation from ethanol. mp 129°-132° C. 1H NMR (360 MHz, D6 -DMSO) δ 1.24 (3H, t, J=7.4 Hz), 3.47 (2H, q, J=7.4 Hz), 5.40 (2H, brs), 6.77-6.83 (1H, m), 7.02-7.08 (2H, m), 7.13 (1H, dd, J=7.8 and 7.7 Hz).

Sources & evidence

ORD record
ord-f491be0a320e405f9eb4071750a4c287
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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