2-(4-Nitrophenylthio)quinoline → 2-(4-Aminophenylthio)quinoline

HRID 55095Notes

Reaction equation

HRID 55095 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)[N:12]=2)=[CH:6][CH:5]=1)([O-])=O>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][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)[N:12]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 189716432-(4-Nitrophenylthio)quinoline

Product 1

HCID 226371302-(4-Aminophenylthio)quinolineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4-Nitrophenylthio)quinoline (0.42 moles, 12.0 g) was hydrogenated in 300 ml DMF over 5.0 g Pd/C for 3 hr at room temperature. The solution was filtered through celite and concentrated. The product was triturated with ether and hexane to yield 2-(4-aminophenylthio)quinoline 10.0 g, 93%.

Workup

  1. filtrationThe solution was filtered through celite
  2. concentrationconcentrated
  3. customThe product was triturated with ether and hexane

Sources & evidence

ORD record
ord-cf4c99fe053f41b9ab5b2ac5ab6a9af3
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Reaction notes

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