1-Methylsulfonylmethyl-3-nitro-5-trifluoromethyl-benzene → 3-(Methylsulfonyl)methyl-5-trifluoromethyl-aniline

HRID 1957957Notes

Reaction equation

HRID 1957957 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([N+:16]([O-])=O)[CH:7]=1)(=[O:4])=[O:3]>CO.[Pd]>[CH3:1][S:2]([CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)[NH2:16])(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 684233041-Methylsulfonylmethyl-3-nitro-5-trifluoromethyl-benzene

Product 1

HCID 592861493-(Methylsulfonyl)methyl-5-trifluoromethyl-aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-methylsulfonylmethyl-3-nitro-5-trifluoromethyl-benzene (520 mg; 2.170 mmol) and 50 mg of Pd/C 10% in methanol (50 ml) was hydrogenated (1 bar) overnight. The reaction mixture was filtered on a celite pad and the obtained solution concentrated in vacuo. The crude was washed with dichloromethane in order to filter salts, coming from the previous reaction. 100 mg (0.395 mmol; 18% yield) were obtained.

Workup

  1. custom(1 bar) overnight
  2. filtrationThe reaction mixture was filtered on a celite pad
  3. concentrationthe obtained solution concentrated in vacuo
  4. washThe crude was washed with dichloromethane in order
  5. filtrationto filter salts
  6. customcoming from the previous reaction
  7. custom100 mg (0.395 mmol; 18% yield) were obtained

Sources & evidence

ORD record
ord-6caa83cd7b8c43509d4ada3f7ce8c58b
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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