Aluminium lithium hydride → 3-(Isobutylamino)-4-nitrobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Add lithium aluminum hydride (4.4 mL, 1 M in tetrahydrofuran) dropwise to a solution of N-[methyl]-N-[methoxy]-3-(isobutylamino)-4-nitrobenzamide (1.18 g, 4.2 mmol) in 20 mL of dry tetrahydrofuran at −78° C. Warm the mixture to −30° C. over 2 hours, and then to 0° C. over 30 minutes. Cool to −70° C. and carefully quench with 30 mL 5% aqueous potassium hydrogensulfate, warm to 0° C., and dilute with ethyl acetate. Separate the phases, dry the organic phase over magnesium sulfate and concentrate under reduced pressure to provide the desired benzaldehyde (70%).

Provenance & Evidence