N-(4-nitrobenzyl)methanesulfonamide → HCID 12822521, compound

HRID 1428709Notes

Reaction equation

HRID 1428709 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CO.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 12822520N-(4-nitrobenzyl)methanesulfonamide

Product 1

HCID 12822521HCID 12822521, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

N-(4-Nitrobenzyl)methanesulfonamide (881 mg, 3.83 mmol) was dissolved in methanol/tetrahydrofuran (1:1, 35 mL). 10% Pd/C (264 mg, 3 eq) 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)methanesulfonamide (352 mg, 46%).

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-3c9ae640203c437e88e89a0d915a67e4
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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