Methyl morpholine oxide → 5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde

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Reaction Steps

To a suspension of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one (780 mg, 1.8 mmol) in methylene chloride (15 mL) was added 4-methylmorpholine N-oxide (316 mg, 2.7 mmol). To the resulting clear solution was added molecular sieves (900 mg) followed by tetrapropylammonium perruthenate (32 mg, 0.09 mmol). The resulting mixture was stirred at rt for 2 h. The mixture was then filtered through silica gel eluting with ethyl acetate. Removal of the solvent and subsequent purification by flash chromatography using 25% acetone/hexane provided 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde as a white solid. 1H NMR (CDCl3, 500 MHz): δ 4.43 (abq, 2H, J=15.5 Hz), 5.37 (s, 1H), 6.66 (s, 1H), 7.30-7.60 (m, 8H), 9.85 (s, 1).

Provenance & Evidence