3-Hydroxybenzaldehyde → 3-[(7-Chloro-2-quinolinyl)methoxy]benzaldehyde

Participants

Reaction Steps

A suspension of 7-chloro-2-(bromomethyl)quinoline (50.5 g, 197 mmol, EP 233,763, Example 4, Step 1), 3-hydroxybenzaldehyde (22.9 g, 188 mmol) and K2CO3 (51.7 g, 375 mmol) in 600 mL of acetone was heated to reflux for 2 h. After cooling down, 200 mL of CH2Cl2 was added and the mixture was filtered through celite with acetone:CH2Cl2 3:1. The title product was purified by flash chromatography on silica with EtOAc:toluene 5:95 to yield 46.64 g, 83%. (Alternatively, the product may be purified by a swish in ether:hexane 7:1).

Provenance & Evidence