Реакция #1162709

Уравнение реакции

sodium hydroxide

ethyl 9-(N-methylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate

→

9-(N-methylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid

Растворители

dioxane

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONdistilled water (100/27 by volume) mixture
2. 2
   ФильтрацияThe light-grey insoluble material is filtered
3. 3
   Промывкаwashed with acetone
4. 4
   ФильтрацияThis aqueous solution is filtered
5. 5
   ДругоеThe precipitate formed
6. 6
   Фильтрацияis filtered
7. 7
   Промывкаwashed with water, with acetone

Методика

8.2 ml of 1N sodium hydroxide solution are added dropwise, under a stream of nitrogen and at a temperature in the region of 20° C., to a suspension of 1 g of ethyl 9-(N-methylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate in a dioxane distilled water (100/27 by volume) mixture. The reaction is continued for 2 hours at the same temperature. The light-grey insoluble material is filtered, washed with acetone and then taken up in 15 ml of distilled water. This aqueous solution is filtered and then acidified to pH 1 with N hydrochloric acid. The precipitate formed is filtered and washed with water, with acetone and then with ethyl ether to result in 0.59 g of the trihydrate of 9-(N-methylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid in the form of a white powder, the melting point of which is greater than 260° C. (Analysis C17H14N4O4.3H2O; % Calculated C: 60.35, H: 4.17, N: 16.56; % Found C: 60.0, H: 4.1, N: 16.3; 1H NMR spectrum in CD3CO2D, T=300K, δ in ppm (300 MHz): 2.7 (3H, s, NCH3), 3.9 (2H, s, CH2CO), 4.1 (2H, s, CH2), 7.2 (1H, d, J=8 Hz, arom. CH), 7.4 (1H, t, J=8 Hz, arom. CH), 7.7 (1H, d, J=8 Hz, arom. CH), 8.5 (1H, s, imidazole H)).

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