4-(4-Nitrophenylthio)quinoline → 4-(4-Aminophenylthio)quinoline

HRID 55071Notes

Reaction equation

HRID 55071 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)[N:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 189716424-(4-Nitrophenylthio)quinoline

Product 1

HCID 189716534-(4-Aminophenylthio)quinolineYield 58.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-nitrophenylthio)quinoline (17.0 mmoles, 4.9 g) was dissolved in 200 ml ethanol and hydrogenated over 5 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 4-(4-aminophenylthio)quinoline 2.5 g, 58%. Mass spec (FD) 253. Calculated for C15H12N2S: C, 71.40; H, 4.79, N, 11.10. Found: C, 1.12; H, 4.93 N, 10.88.

Workup

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

Sources & evidence

ORD record
ord-bf218205d9a34cf88976b751baf5848d
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Reaction notes

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