1-(4-Nitrophenylthio)naphthalene → Benzenamine, 4-(1-naphthalenylthio)-

HRID 2395334Notes

Reaction equation

HRID 2395334 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 189716701-(4-Nitrophenylthio)naphthalene

Product 1

HCID 11322702Benzenamine, 4-(1-naphthalenylthio)-Yield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Nitrophenylthio)naphthalene (39.0 mmoles, 11.0 g) was dissolved in 200 ml ethyl acetate and hydrogenated over 8 g of 5% Pd/C at 40 psi for 1 hr at room temperature. The solution was filtered through celite and the solvent removed to yield 1-(4-aminophenylthio)naphthalene 9.0 g, 92%. Mass spec (FD) 251. Calculated for C15H17NS: C, 76.46; H, 5.21, N, 5.57 Found: C, 76.71; H, 5.39; N, 5.47.

Workup

  1. filtrationThe solution was filtered through celite
  2. customthe solvent removed

Sources & evidence

ORD record
ord-0a840c089d8d4b3192ad914ed6595eff
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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