Bond cleavage

Catalysis

Engineering

Geotechnical engineering

Oxidative cleavage

Enamine

Cleavage (geology)

Medicinal chemistry

Combinatorial chemistry

Organic chemistry

Fracture (geology)

Chemistry

Ether

Pyridine

Synlett

A scaleable synthesis of 3-hydroxy-1,5-naphthyridine-4-carbaldehyde is described. 3-Amino-5-methoxy-4-methyl-pyridine underwent the Skraup reaction to give the corresponding 1,5-naphthyridine which, upon treatment with DMF-DMA in the presence of catalytic amount of LiOH, provided the N,N-dimethyl enamine intermediate. Oxidative cleavage, followed by removal of the methyl ether afforded the titled product.

A Scaleable Synthesis of 3-Hydroxy-1,5-naphthyridine-4-carbaldehyde