Dimethyl Sulfoxide → 1-[1-(Methoxyimino)-2,3-dihydro-1H-inden-5-yl]-2-(pyridin-4-yl)ethane-1,2-dione

Participants

Reaction Conditions

Reaction Steps

To a mixture of DMSO (43 ml, 0.56 mol) and dichloromethane (800 ml) at −70° C. under argon, was added oxalyl chloride (71.4 g) and then a solution of the product of Step 3 (55 g, 0.185 mol) in a mixture of dichloromethane/DMSO (1000 ml/60 ml) over 2 hours at −60° C. After stirring for 2 hours at −60° C., triethylamine (154 ml) was added dropwise and the mixture then allowed to warm to room temperature overnight. The reaction mixture was then quenched with water, the organic phase separated then washed with water, dried (Na2SO4) and concentrated to yield the title compound (51 g, 94%) as a yellow solid. 1H NMR (CDCl3) 8.87 (2H, d), 7.89–7.77 (5H, m), 4.03 (3H, s), 3.09 (2H, m), 2.93 (2H, m).

Provenance & Evidence