Water → 2-Amino-4-phenylsulfonylphenol

HRID 2224059Notes

Reaction equation

HRID 2224059 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-])=O)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>[Pd].CCO>[NH2:17][C:12]1[CH:11]=[C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:15]=[CH:14][C:13]=1[OH:16]

Participants

5

Reactant 2

HCID 962WaterHCID 159333442-Nitro-4-phenylsulfonylphenol

Product 1

HCID 133660362-Amino-4-phenylsulfonylphenolYield 47.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Benzenesulfonyl-2-nitro-phenol (6.37 g, 22.8 mmol), Pd/C (5%, 3 mg) and 1 mL of water were added to a flask, after which 45 mL of EtOH was added. The reaction mixture was stirred and purged with H2 (1 Atm). The reaction mixture was stirred under H2 for 4 hours, then filtered through celite. The filtrate was concentrated in vacuo to yield a crude oil, which was purified by flash chromatography (0-15% “magic base” (6:1:0.1 methylene chloride:methanol:ammonia) in dichloromethane) to afford 2-amino-4-benzenesulfonyl-phenol (2.695 g, 39%). MS: 250 (M+H)+.

Workup

  1. custompurged with H2 (1 Atm)
  2. stirringThe reaction mixture was stirred under H2 for 4 hours
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto yield a crude oil, which
  6. customwas purified by flash chromatography (0-15% “magic base” (6:1:0.1 methylene chloride:methanol:ammonia) in dichloromethane)

Sources & evidence

ORD record
ord-d64eb76ce91e4fe4b0eb25306d090014
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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