3-Amino-6-chloro-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide → 3-Amino-N-ethyl-2-hydroxy-N-methoxybenzenesulfonamide

HRID 1024575Notes

Reaction equation

HRID 1024575 reaction equation
[NH2:1][C:2]1[C:3]([OH:17])=[C:4]([S:9]([N:12]([O:15][CH3:16])[CH2:13][CH3:14])(=[O:11])=[O:10])[C:5](Cl)=[CH:6][CH:7]=1.[H][H]>CCO.[Pd]>[NH2:1][C:2]1[C:3]([OH:17])=[C:4]([S:9]([N:12]([CH2:13][CH3:14])[O:15][CH3:16])(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 866386363-Amino-6-chloro-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 866386403-Amino-N-ethyl-2-hydroxy-N-methoxybenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A dispersion of 10% Pd/C (200 mg) in a solution of 3-amino-6-chloro-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide (Int. FA step 2) (400 mg, 1.425 mmol) in EtOH (50 ml) was placed under a positive pressure of hydrogen at 0.5 bar above atmospheric pressure. After 5 hours, the catalyst was removed by filtration through Celite® (filter material), and the filtrate was reduced in vacuo. The resulting solid was used in the next step, without further purification.

Workup

  1. customthe catalyst was removed by filtration through Celite® (filter material)
  2. customThe resulting solid was used in the next step, without further purification

Sources & evidence

ORD record
ord-5ae95c72e6694c1f951c73782bc021f3
Source dataset
uspto-grants-2014_05
Patent number
US08722925B2

Reaction notes

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