(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine → 6-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

Participants

Reaction Steps

A modification of the general method described in Part B of Example 46 was followed using 6-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine (5.1 g, 12 mmol) in lieu of (7-benzyloxy-3-nitro-quinolin-4-yl)-(2-phenoxyethyl)amine. The reaction was maintained under hydrogen pressure (49 psi, 3.4×105 Pa) for three hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol (100 mL) and chloroform (50 mL). The filtrate was concentrated under reduced pressure to provide 6-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine as a yellow oil, which was used without purification.

Provenance & Evidence