Hydrochloric Acid → 5-(3-Hydroxypropyl)-1-{[4-(methyloxy)phenyl]methyl}-1,2-dihydro-3,6-pyridazinedione

Participants

Reaction Conditions

Reaction Steps

Butyl 3-(2-{[4-(methyloxy)phenyl]methyl}-3,6-dioxo-1,2,3,6-tetrahydro-4-pyridazinyl)propanoate (0.56 g, 1.56 mmol) was dissolved in dry THF (30 ml). The solution under argon was cooled to −30° C., treated dropwise with a 1M solution of lithium aluminium hydride in THF (1.8 ml, 1.8 mmol), allowed to warn gradually to 0° C. and stirred in an ice bath for 30 minutes. 2M Hydrochloric acid was added until pH 3 was obtained, and the mixture was partitioned between water and ethyl acetate. The aqueous was re-extracted with ethyl acetate and the combined organic solution dried and evaporated. Chromatography of the residue on silica, eluting with ethyl acetate, gave the product as a white solid (300 mg, 67%).

Provenance & Evidence