Sodium Iodide → 4-tert-Butyl-5-chloro-3,4-dihydro-1H-quinoxalin-2-one

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Reaction Conditions

Reaction Steps

Bromoacetyl bromide (2.8 ml, 32 mmol) was added drop wise to a solution of N*2*-tert-butyl-3-chlorobenzene-1,2-diamine from Example 12B (4.1 g, 21 mmol) and diisopropylethylamine (11 ml, 63 mmol) in THF (75 ml) while cooling to −78° C. The mixture was allowed to warm to room temperature over 18 h and the solvent was evaporated. Chloroform was added and the mixture was washed with sodium hydrogen carbonate, dried and evaporated. To the residue were added acetonitrile (90 ml), diisopropylethylamine (5.6 ml, 32 mmol) and sodium iodide (3.2 g, 21 mmol). The mixture was heated at reflux for 18 h, cooled and evaporated. The residue was taken up in chloroform, washed with water, dried and evaporated. The residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 100:0 to 50:50) to give an orange solid; yield 1.5 g, 29%.

Provenance & Evidence