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N-(2-methyl-4-nitrobenzyl)methanesulfonamide → N-(4-amino-2-methylbenzyl)methanesulfonamide

HRID 1428761
Notes
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Reaction equation

HRID 1428761 reaction equation
[CH3:1][C:2]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:3]=1[CH2:4][NH:5][S:6]([CH3:9])(=[O:8])=[O:7]>O1CCCC1.C(O)C.[Pd]>[NH2:14][C:12]1[CH:11]=[CH:10][C:3]([CH2:4][NH:5][S:6]([CH3:9])(=[O:8])=[O:7])=[C:2]([CH3:1])[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 86679389N-(2-methyl-4-nitrobenzyl)methanesulfonamide

Product 1

HCID 86679390N-(4-amino-2-methylbenzyl)methanesulfonamideYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2-methyl-4-nitrobenzyl)methanesulfonamide (100 mg, 0.409 mmol) in tetrahydrofuran and ethanol as co-solvent were added 10% Pd/C (40 mg). The mixture was charged with H2 (gas) balloon. The resulting mixture was stirred for 24 h, then filtered using celite. The filtrate removed in vacuo. The crude was purified by column chromatography. N-(4-Amino-2-methylbenzyl)methanesulfonamide (61 mg) was obtained as 70% yield.

Workup

  1. additionThe mixture was charged with H2 (gas) balloon
  2. filtrationfiltered
  3. customThe filtrate removed in vacuo
  4. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-0e2af21424fc4ce3b20a39e69cbb1a37
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937092B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes