Ethyl Acetate → 2-Ethyl-5-(methylsulfonyl)aniline

HRID 575777Notes

Reaction equation

HRID 575777 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][C:4]=1[N+:13]([O-])=O)[CH3:2].CC(=O)OCC>[Pd].CO>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:5][C:4]=1[NH2:13])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 582661211-Ethyl-4-methylsulfonyl-2-nitrobenzene

Product 1

HCID 283558962-Ethyl-5-(methylsulfonyl)anilineYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound of step 1 (0.6 g, 2.6 mmol) and palladium on carbon (0.18 g) in CH3OH (20 mL) was hydrogenated at 1 atm. for 6 h. Silica gel chromatography (PE:EA=6:1) gave the title compound (0.49 g, 94%) as a brown liquid.

Sources & evidence

ORD record
ord-5c34382e21f54caf975beac099012143
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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