2-Methyl-1-(methylsulphonylaminocarbonyl)-5-nitrobenzene → 2-Methyl-1-(methylsulphonylaminocarbonyl)-5-aminobenzene

HRID 2379357Notes

Reaction equation

HRID 2379357 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[O:12]>[Pd].O.C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[O:12]

Participants

5

Reactant 1

HCID 189577932-Methyl-1-(methylsulphonylaminocarbonyl)-5-nitrobenzene

Product 1

HCID 189577552-Methyl-1-(methylsulphonylaminocarbonyl)-5-aminobenzeneYield 79.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 2-methyl-1-(methylsulphonylaminocarbonyl)-5-nitrobenzene (3 g, 11.6 mmol), 10% palladium on carbon (0.3 g, 10% (w/w)) in water (2 ml) and ethanol (100 ml), the title compound (2.1 g, 79%) was afforded as a pale yellow crystalline solid. mp 174°-176° C. 1H NMR (360 MHz, D6-DMSO) δ 2.17 (3H, s), 3.32 (3H, s), 6.61 (1H, dd, J=8.1 and 2.5 Hz), 6.67 (1H, d, J=2.4 Hz), 6.92 (1H, d, J=8.2 Hz).

Sources & evidence

ORD record
ord-eff80f159c5843f389648c09d15c045b
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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