Cleavage (geology)

Organic chemistry

Combinatorial chemistry

Engineering

Catalysis

Medicinal chemistry

Chemistry

Geotechnical engineering

Enamine

Pyridine

Ether

Fracture (geology)

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