Reaction #83346

Reaction equation

2-Chloro-6-methoxyquinoline

4-aminothiophenol

dimethylaminopyridine

→

2-(4-aminophenylthio)-6-methoxyquinoline

Solvents

ethanol

Conditions

Workup

1. 1
   Othercondensed
2. 2
   Otherpurified by HPLC over silica gel
3. 3
   Washeluted with 25-30% ethyl acetate/hexane

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.

Source