N-(2-fluoro-4-nitrobenzyl)methanesulfonamide → N-(4-amino-2-fluorobenzyl)methanesulfonamide

HRID 1428739Notes

Reaction equation

HRID 1428739 reaction equation
[F: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]([F:1])[CH:13]=1

Participants

5

Reactant 1

HCID 86679366N-(2-fluoro-4-nitrobenzyl)methanesulfonamide

Product 1

HCID 86679367N-(4-amino-2-fluorobenzyl)methanesulfonamideYield 86.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2-fluoro-4-nitrobenzyl)methanesulfonamide (250 mg, 1.007 mmol) in tetrahydrofuran and ethanol as co-solvent were added 10% Pd/C (25 mg). The mixture was charged with H2 (gas) balloon. The resulting mixture was stirred for 15 h, then filtered by using celite. The filtrate was removed in vacuo. The crude was purified by column chromatography. N-(4-Amino-2-fluorobenzyl)methanesulfonamide (190 mg) was obtained as 86% yield.

Workup

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

Sources & evidence

ORD record
ord-17862222d0ab44c58a5ceb989df33303
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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