2-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide → 3-amino-N-(2-hydroxyethyl)benzenesulfonamide

HRID 1259045Notes

Reaction equation

HRID 1259045 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[S:11]([NH:14][CH2:15][CH2:16][OH:17])(=[O:13])=[O:12]>CO.[Pd]>[NH2:8][C:5]1[CH:4]=[C:3]([S:11]([NH:14][CH2:15][CH2:16][OH:17])(=[O:13])=[O:12])[CH:2]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 145740892-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide

Product 1

HCID 4587823-amino-N-(2-hydroxyethyl)benzenesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide (1.00 g, 3.57 mmol) was dissolved in methanol (35 ml) and placed under an atmosphere of nitrogen prior to the addition of 10% Pd/C (10 Wt %, 100 mg) in one portion. The reaction was evacuated, placed under an atmosphere of hydrogen (1 bar) and stirred vigorously overnight. The reaction was filtered through celite and the filtrate was concentrated in vacuo to afford the named product (0.77 g, 100%); LCMS Rt=1.44 min, m/z (ES+) 217 (M+H).

Workup

  1. customThe reaction was evacuated
  2. filtrationThe reaction was filtered through celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-98e97ed5a858492589e1c3ff766b0a92
Source dataset
uspto-grants-2013_06
Patent number
US08466201B2

Reaction notes

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