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

HRID 516922Notes

Reaction equation

HRID 516922 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>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

4

Reactant 1

HCID 866386363-Amino-6-chloro-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

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 hyrdrogen 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-4d430165cc83427dae17bb0512604483
Source dataset
uspto-grants-2015_08
Patent number
US09115087B2

Reaction notes

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