N-(4-nitrobenzyl)ethanesulfonamide → N-(4-aminobenzyl)ethanesulfonamide

HRID 1428766Notes

Reaction equation

HRID 1428766 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CO.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 47372696N-(4-nitrobenzyl)ethanesulfonamide

Product 1

HCID 39243426N-(4-aminobenzyl)ethanesulfonamideYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Nitrobenzyl)ethanesulfonamide (776 mg, 3.18 mmol) was dissolved in methanol and tetrahydrofuran (1:1, 35 mL). 10% Pd/C (264 mg, 3 equiv) was added to it. The resulting mixture was stirred at room temperature for overnight under H2. TLC showed complete consumption of starting material. The mixture was filtered through celite bed and the filterate was concentrated under reduced pressure. The crude was purified by column chromatography to give N-(4-aminobenzyl)ethanesulfonamide (504 mg, 74%).

Workup

  1. customconsumption of starting material
  2. filtrationThe mixture was filtered through celite bed
  3. concentrationthe filterate was concentrated under reduced pressure
  4. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-ff8e9342d21b48bbaee42d5f3ada9961
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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