4-Aminothiophenol → 2-(4-Aminophenylthio)-4-ethoxycarbonylquinoline

HRID 55062

Reaction equation

HRID 55062 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.C(O)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][C:2]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 145104-AminothiophenolHCID 230586Ethyl 2-chloroquinoline-4-carboxylate

Product 1

HCID 189716462-(4-Aminophenylthio)-4-ethoxycarbonylquinolineYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

2-Chloro-4-ethoxycarbonylquinoline (0.024 moles, 5.56 g), 4-aminothiophenol (0.024 moles, 3.0 g) and 4-dimethylaminopyridine (0.024 moles, 2.9 g) were stirred in 250 ml ethanol for 3 days. The reaction mixture was filtered, concentrated, ethyl acetate added, washed with water and dried over sodium sulfate. The solution was concentrated and the product purified by HPLC over silica gel eluted with 25% ethyl acetate/hexane to yield 2-(4-aminophenylthio)-4-ethoxycarbonylquinoline 2.8 g, 36%. Mass Spec (FD) 324. Calculated for C18H16N2O2S: C, 66.64; H, 4.97; N, 8.63. Found: C, 66.50; H, 5.00 N, 8.54.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionethyl acetate added
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated
  7. customthe product purified by HPLC over silica gel
  8. washeluted with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-603b04cd056d463f8fd093942204d27e
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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