Aluminium lithium hydride → 1-(4-Methoxybenzyl)-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-methoxybenzyl)-N-methoxy-N-methyl-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carboxamide (3) (4.60 g, 13.8 mmol) in THF (50.0 mL) was treated with 1.0 M LAH in THF (15 mL, 15 mmol) at −78° C. The mixture was stirred at 0° C. for 1 h then quenched carefully at 0° C. with MeOH (1.0 mL), followed by water (1.0 mL) and 1 M aq HCl (1.0 mL). The resulting suspension was filtered and the filtrate was concentrated in vacuo to give 1-(4-methoxybenzyl)-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carbaldehyde as a pale yellow solid. MS (ESI, pos. ion) m/z: 274 (M+1).

Provenance & Evidence