Acetic Acid → (4-Amino-3-methylphenyl)methanesulfonamide

HRID 907462Notes

Reaction equation

HRID 907462 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][S:12]([NH2:15])(=[O:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.CCO.CC(O)=O>[Pd].C1COCC1>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][S:12]([NH2:15])(=[O:13])=[O:14])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 44245339(3-Methyl-4-nitrophenyl)methanesulfonamide

Product 1

HCID 44244999(4-Amino-3-methylphenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The sulfonamide 14 (31.7 g, 138 mmol) was dissolved into boiling EtOH (600 ml) containing some AcOH (80 ml). To this solution was added 10% Pd/C (1.4 g) and this mixture was stirred under hydrogen (40 psi) for 3 h. THF (50 ml) was then added and this mixture heated to dissolve the precipitated product. This solution was filtered through celite and concentrated. The resulting solid was triturated with ether:hexane 1:1 (200 ml) to yield 27.28 g (99%) of pure 15.

Workup

  1. temperaturethis mixture heated
  2. dissolutionto dissolve the precipitated product
  3. filtrationThis solution was filtered through celite and
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with ether:hexane 1:1 (200 ml)
  6. customto yield 27.28 g (99%) of pure 15

Sources & evidence

ORD record
ord-243bf4d6210c4abb926f1db28f125136
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

Loading…