4-(Trifluoromethyl)benzylamine → 3-Chloro-4-hydroxybenzoic Acid {2-Methoxy-4-[2-(4-Trifluoromethylbenzylamino)ethoxy]-benzylidene}hydrazide

Participants

Reaction Steps

This compound was prepared analogously to the compound described in the previous example starting from resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (resin—[building block 1]) (2 g, ˜2 mmoles), 4-(2-bromoethoxy)-2-methoxybenzaldehyde ([building block 2]) (0.73 g, 1.5 equivs.), and 4-trifluoromethylbenzylamine ([building block 3]) (3.3 g, 10 equivs.). After cleavage with 50% trifluoroacetic acid, the residue (1 g) was purified by column chromatography on silica gel (20 g) eluting with a mixture of 25% aq. ammonia, ethanol and dichloromethane (1:9:115). This afforded 130 mg of the title compound.

Provenance & Evidence