Ethyl Acetate → 2-(4-Aminophenylthio)naphthalene

HRID 55076Notes

Reaction equation

HRID 55076 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 189716852-(4-Nitrophenylthio)naphthalene

Product 1

HCID 189716452-(4-Aminophenylthio)naphthaleneYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-nitrophenylthio)naphthalene (9.2 moles, 2.6 g) was dissolved in 50 ml ethanol and 20 ml ethyl acetate and hydrogenated for 16 hrs at room temperature over 1.0 g 5% Pd/C. The solution was filtered through celite and concentrated to yield 2-(4-aminophenylthio)naphthalene 1.1 g, 47%.

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2d5e005bea104a578197412c06cc98bd
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Reaction notes

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