Methanol → (4-Aminophenyl)methanesulfonic acid

HRID 905921Notes

Reaction equation

HRID 905921 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([OH:12])(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.CO>[Pd].O>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([OH:12])(=[O:10])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 316247(4-Nitrophenyl)methanesulfonic acid

Product 1

HCID 423124(4-Aminophenyl)methanesulfonic acidYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A 250 ml of Par hydrogenation bottle was charged 4-Nitrobenzyl Sulfonic Acid (6.80 g, 31.34 mmol), 10% Pd/C (0.4 g), CH3OH (150 ml) with few drop of water, and purged with hydrogen. The reaction mixture was shaken with 20 psi H2 over night. The catalyst was removed by filtration through celite and the solvent was evaporated. The crude compound was co-evaporated three times with 3×50 ml of water and crystallized with water/THF/EtAc/Toluene (1:10:10:100) to give 5.3 g (91%) of the title compound. 1H NMR (D2O), 7.28 (dd, 2H, J=2.2, 4.3 Hz), 6.95 (dd, 2H, J=2.2, 4.3 Hz), 4.10 (s, 2H); 13C NMR 134.30, 127.10, 121.04, 120.42, 59.14; MS m/z−186.35 (M−H).

Workup

  1. custompurged with hydrogen
  2. customThe catalyst was removed by filtration through celite
  3. customthe solvent was evaporated
  4. customcrystallized with water/THF/EtAc/Toluene (1:10:10:100)

Sources & evidence

ORD record
ord-0953ecca2e3e497684987a406774e360
Source dataset
uspto-grants-2011_09
Patent number
US08012978B2

Reaction notes

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