N-Methylmorpholine N-oxide monohydrate → 4-(Cyclohexylamino)-3-nitrobenzaldehyde

Participants

Reaction Steps

To a solution of 4-cyclohexylamino-3-nitrobenzyl alcohol (21.0 g, 83 mmol) in DCM (300 mL) was added powdered 4A molecular sieves (15 g) and N-methyl morpholine-N-oxide monohydrate (10.8 g, 92.2 mmol). Tetra-n-propylammonium perruthenate (VII) (2.91 g, 8.28 mmol) was then added in a single portion. An initial exotherm was controlled using an ice bath, and then the reaction mixture was stirred at room temperature for 18 hr. The mixture was then reduced to ˜100 mL by evaporation, and loaded onto a column of silica (400 g). The column was eluted with acetone:hexane 1:3 and the spot at 0.30 was collected, affording 4-cyclohexylamino-3-nitrobenzaldehyde as a yellow solid. (11.0 g, 44.3 mmol): 1H NMR (CDCl3, 300 MHz) δ 9.60 (s, 1H), 8.32 (s, 1H), 7.71 (d, J=10 Hz, 1H), 6.73 (d, J=10 Hz, 1H) 3.46-3.32 (m, 1H), 1.90-1.15 (m, 10H).

Provenance & Evidence