Sodium Hydroxide → HCID 66875499, compound

Participants

Reaction Steps

A pressure vial containing a mixture of 4-chloro-5-(methyl-phenyl-amino)-2H-pyridazin-3-one (158.7 mg, 0.67 mmol), water (10 mL), and a 2N aqueous solution of sodium hydroxide (0.37 mL) was treated with 10% palladium on carbon (15.8 mg, 10% weight of 4-chloro-5-(methyl-phenyl-amino)-2H-pyridazin-3-one). The reaction was then pressurized with hydrogen (50 psi), where it shook overnight. The resulting reaction mixture was filtered through a pad of diatomaceous earth and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solution was acidified to pH 1-2 with a 1N aqueous hydrochloric acid solution and then extracted into methylene chloride (2×25 mL). Thin layer chromatography indicated the presence of starting material. The reaction was re-exposed to the same hydrogenation conditions. The reaction was hydrogenated (50 psi) for 2 d. After this time, the resulting reaction mixture was filtered through a pad of diatomaceous earth and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solution was acidified to pH 1-2 with a 1N aqueous hydrochloric acid solution and then extracted into methylene chloride (3×25 mL). The combined organics were dried over magnesium sulfate, filtered, rinsed, and concentrated in vacuo. Silica gel column chromatography (AnaLogix 24 g, 50-100% ethyl acetate/hexanes) afforded 5-(methyl-phenyl-amino)-2H-pyridazin-3-one (75.8 mg, 56%) as a yellow solid.

Provenance & Evidence