2-(2-Nitro-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzenesulfonic acid, ammonium salt → 2-(2-Amino-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzenesulfonic acid

HRID 1416352Notes

Reaction equation

HRID 1416352 reaction equation
[NH4+].[N+:2]([C:5]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:18])([CH3:17])[CH2:15][CH3:16])=[CH:10][C:9]=1[S:19]([O-:22])(=[O:21])=[O:20])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:2][C:5]1[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:18])[CH2:15][CH3:16])=[CH:10][C:9]=1[S:19]([OH:22])(=[O:21])=[O:20]

Participants

4

Reactant 1

HCID 1317192122-(2-Nitro-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzenesulfonic acid, ammonium salt

Product 1

HCID 99091322-(2-Amino-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzenesulfonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Nitro-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzenesulfonic acid, ammonium salt (620 mg) was mixed in ethyl acetate (50 ml) and palladium on carbon (202 mg) was added under argon. The mixture was hydrogenated in a Parr bottle at 55 psi for two hours. The sample was filtered to remove the catalyst, mixed with methanol and degassed for several hours to yield the title compound. 1H NMR (250 MHz, CD3OD) ∂ 7.95 (d, 1H), 7.30 (dd, 1H), 7.05 (dd, 2H), 6.85 (dd, 1H), 6.75 (d, 1H), 1.65 (q, 3H), 1.25 (s, 6H), 0.65 (t, 2H).

Workup

  1. filtrationThe sample was filtered
  2. customto remove the catalyst
  3. additionmixed with methanol
  4. customdegassed for several hours

Sources & evidence

ORD record
ord-9c17cef3614b437999b62fbc8ac438f2
Source dataset
uspto-grants-1999_06
Patent number
US05912270

Reaction notes

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