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

HRID 2395324Notes

Reaction equation

HRID 2395324 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-eb3b450a9b7f46d590bbedf2c022e442
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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