Methane → HCID 9859557, compound

Participants

Reaction Conditions

Reaction Steps

0.86 g of sodium borohydride is added over 5 minutes to a stirred suspension of 2.4 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4,10-dione in 75 ml of methanol at a temperature between 25° C. and 35° C. After stirring for 30 minutes at 20° C., the insoluble material is isolated by filtration, washed with 10 ml of methanol and dried under reduced pressure (15 mmHg; 2 kPa) at 20° C. The product obtained (2.3 g) is dissolved in 100 ml of dimethylformamide and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered and the filter is then washed with 20 ml of dimethylformamide. The filtrate and the washings are combined and 240 ml of distilled water are added. The solid is filtered off, washed twice with 40 ml in total of distilled water and with 20 ml of acetone and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 1.9 g of 10-hydroxy-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one are thus obtained, melting at 290° C. (decomposition) [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): 5.65 (d, J=8.5 Hz, 1H: CH--O--); 6.17 (d, J=8.5 Hz, 1H: --OH); 7.33 and 7.41 (2dt, J=7.5 and 1 Hz, 1H each: --H7 and --H8); 7.57 and 7.77 (2dd, J=7.5 and 1 Hz, 1H each: --H6 and --H9); 7.58 and 7.93 (2s broad, 1H each: --H of the imidazole); 12.40 (cplx, 1H: --NH--)].

Provenance & Evidence