2-Nitro-5-(phenylsulfonyl)phenol → HCID 14053206, compound

HRID 2224054Notes

Reaction equation

HRID 2224054 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([N+:17]([O-])=O)=[C:14]([OH:16])[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[NH2:17][C:13]1[CH:12]=[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][C:14]=1[OH:16]

Participants

4

Reactant 1

HCID 27996822-Nitro-5-(phenylsulfonyl)phenol

Product 1

HCID 14053206HCID 14053206, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a 1 liter flask was added 500 mg of a 5% dispersion of palladium metal on charcoal. The solid was wetted with 40 mL of ethanol and the flask was charged with a solution of 5-benzenesulfonyl-2-nitro-phenol (17.35 g., 62.1 mmol) in 350 mL ethanol. The flask was purged with hydrogen gas and a pressure of 1 Atm was maintained for 2 hours. The reaction mixture was filtered through celite, the filtrate concentrated in vacu, and the resulting residue was purified by flash (1:1:2 of “magic base” (6:1:0.1 methylene chloride:methanol:ammonia):CH2Cl2:hexanes.) The resulting solid was recrystallized from 300 mL EtOAc to give 7.68 g (31 mmol, 50%) of 2-amino-5-benzenesulfonyl-phenol as crystalline solid. MS: 250 (M+H)+.

Workup

  1. customThe flask was purged with hydrogen gas
  2. temperaturea pressure of 1 Atm was maintained for 2 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate concentrated in vacu
  5. customthe resulting residue was purified by flash (1:1:2 of “magic base” (6:1:0.1 methylene chloride:methanol:ammonia):CH2Cl2:hexanes.) The resulting solid
  6. customwas recrystallized from 300 mL EtOAc

Sources & evidence

ORD record
ord-5da3a1ed517b4dfd8fa658379630a8d0
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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