4-Aminothiophenol → 2-(4-Aminophenylthio)-6-methoxyquinoline

HRID 55068

Reaction equation

HRID 55068 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.CN(C1C=CC=CN=1)C>C(O)C>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[N:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 218852-DimethylaminopyridineHCID 836472-Chloro-6-methoxyquinoline

Product 1

HCID 189716622-(4-Aminophenylthio)-6-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-methoxyquinoline (52.0 mmoles, 10.0 g), 4-aminothiophenol (52.0 mmoles, 6.5 g) and dimethylaminopyridine (52.0 mmoles, 6.3 g) were stirred for 16 hr in 250 ml ethanol. The reaction was condensed and purified by HPLC over silica gel eluted with 25-30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)-6-methoxyquinoline. 8.5 g, 58% product. Mass spec (FD) 282. Calculated for C16H14N2OS: C, 68.06; H, 5.00, N, 9.92. Found: C, 68.04; H, 4.97; N, 10.02.

Workup

  1. customcondensed
  2. custompurified by HPLC over silica gel
  3. washeluted with 25-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-08c795c675d44ec988099b77cf02e9b6
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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