Acetamide, N-[4-(2-quinolinylmethoxy)phenyl]- → 4-(Quinolin-2-ylmethoxy)aniline

Participants

Reaction Steps

A suspension of N-acetyl-4-(quinolin-2-ylmethoxy)aniline (Step 1, 108.9 g) in 1 L of 95% EtOH containing 10M KOH (120 mL) was heated at reflux under nitrogen in a heating mantle. When the hydrolysis was complete (approx. 36 h), the reaction mixture was cooled and EtOH was partially removed under vacuum. The mixture was then diluted with H2O (200 mL) and the fine off-white crystals were collected and thoroughly rinsed with water. The material, after air-drying, yielded 4-(quinolin-2-ylmethoxy)aniline which was used as such in the next step.

Provenance & Evidence