Methyl iodide → HCID 136351323, compound

Participants

Reaction Steps

0.1 g of sodium is dissolved in 3 ml of liquid ammonia at -33° C., followed by portionwise addition of 0.3 g of 10-hydroxyimino-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one. After stirring for 30 minutes, 0.3 g of methyl iodide is added dropwise and the stirring is continued for 4 hours at the same temperature and then for 16 hours while allowing the temperature to return gradually to 20° C. The solid obtained is suspended in a solution of 0.25 g of ammonium chloride in 20 ml of distilled water and, after stirring for 15 minutes, it is filtered and washed with distilled water. The solid obtained is suspended in 50 ml of boiling ethanol, filtered at 20° C., washed twice with 10 ml in total of ethyl ether and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.2 g of 10-methoxyimino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained as a 95/5 mixture of the E and Z forms, subliming at 310° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 4.22 (s, 3H: =NOCH3); 7.37 and 7.50 (2 broad t, J=8 Hz, 1H each: --H 7 and --H 8); 7.57 and 8.01 (2s, 1H each: --H of the imidazole); 7.76 and 8.00 (2 broad d, J=8 Hz, 1H each: --H 6 and --H 9); from 12.50 to 13.00 (broad mult., 1H: --CONH--)).

Provenance & Evidence