N-(2-hydroxyethyl)-2-nitrobenzenesulfonamide → 2-amino-N-(2-hydroxyethyl)benzenesulfonamide

HRID 1259042Notes

Reaction equation

HRID 1259042 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O)(=[O:7])=[O:6]>CO.[Pd]>[NH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([NH:4][CH2:3][CH2:2][OH:1])(=[O:7])=[O:6]

Participants

4

Reactant 1

HCID 3102011N-(2-hydroxyethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 4587812-amino-N-(2-hydroxyethyl)benzenesulfonamideYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(2-Hydroxyethyl)-2-nitrobenzene sulfonamide (1.25 g, 5.08 mmol) was dissolved in methanol (50 ml) and placed under an atmosphere of nitrogen prior to the addition of 10% Pd/C (10 Wt %, 125 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 (0.88 g, 80%); LCMS Rt=2.05 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-82d6c8e793454617bfba53602c5a6878
Source dataset
uspto-grants-2013_06
Patent number
US08466201B2

Reaction notes

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