1-(ethylamino)propan-2-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 50% suspension of 1.5 g sodium hydride in 100 ml tetrahydrofuran, 3 g ethyl-(2-hydroxypropyl)amine are added; this is stirred at room temperature for 30 minutes, thereafter 4.5 g of 3-chloro-6-triphenylmethylazopyridazine are added. Stirring is maintained for 5 minutes, the organic phase is washed with a saturated solution of sodium chloride, rendered anhydrous and evaporated to dryness under a vacuum. The residue is taken up with ethyl alcohol, diluted with water, and the precipitate is collected under a vacuum which is then triturated with diisopropyl ether to yield 4 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine melting at 137° C. (with decomposition). A solution of 3 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine in 300 ml ethyl alcohol and 50 ml tetrahydrofuran containing 300 mg 5% palladium on carbon is hydrogenated at room temperature and pressure. The catalyst is filtered out, then the residue is evaporated and triturated with diethyl ether to yield 2.5 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine melting at 122° C. (with decomposition). A solution of 2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine in 100 ml absolute ethyl alcohol is mixed with 2.5 ml concentrated hydrochloric acid and stirred for 15 minutes at room temperature. This is evaporated under a vacuum and the residue taken up with isopropyl alcohol. This is diluted with diisopropyl ether to yield 1.2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting at 208°-212° C. (with decomposition). Stirring is maintained for 5 minutes the organic phase is washed with a saturated solution of sodium chloride evaporated to dryness under a vacuum diluted with water the precipitate is collected under a vacuum which is then triturated with diisopropyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 50% suspension of 1.5 g sodium hydride in 100 ml tetrahydrofuran, 3 g ethyl-(2-hydroxypropyl)amine are added; this is stirred at room temperature for 30 minutes, thereafter 4.5 g of 3-chloro-6-triphenylmethylazopyridazine are added. Stirring is maintained for 5 minutes, the organic phase is washed with a saturated solution of sodium chloride, rendered anhydrous and evaporated to dryness under a vacuum. The residue is taken up with ethyl alcohol, diluted with water, and the precipitate is collected under a vacuum which is then triturated with diisopropyl ether to yield 4 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine melting at 137° C. (with decomposition). A solution of 3 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine in 300 ml ethyl alcohol and 50 ml tetrahydrofuran containing 300 mg 5% palladium on carbon is hydrogenated at room temperature and pressure. The catalyst is filtered out, then the residue is evaporated and triturated with diethyl ether to yield 2.5 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine melting at 122° C. (with decomposition). A solution of 2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine in 100 ml absolute ethyl alcohol is mixed with 2.5 ml concentrated hydrochloric acid and stirred for 15 minutes at room temperature. This is evaporated under a vacuum and the residue taken up with isopropyl alcohol. This is diluted with diisopropyl ether to yield 1.2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting at 208°-212° C. (with decomposition). Stirring is maintained for 5 minutes the organic phase is washed with a saturated solution of sodium chloride evaporated to dryness under a vacuum diluted with water the precipitate is collected under a vacuum which is then triturated with diisopropyl ether

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-Ethylamino-2-propanol is diacetylated according to the method of W. J. Bailey and C. N. Bird [J. Org. Chem. 23, 996 (1958)], and then the ester group of the product is hydrolyzed to free hydroxy group in a 10% ethanolic potassium hydroxide solution at room temperature. The resulting 1-(N-ethyl-acetamido)-2-propanol, bp.: 100°-110° C./53.3 Pa, is chlorinated as described in Step b) of Example 31 under boiling the mixture for 3 hours, and the resulting 1-(N-ethylacetamido)-2-chloro-propane, b.p.: 102°-110° C./53.3 Pa (6.0 g, 36.7 mmoles), is reacted with 9.3 ml (9.1 g, 75 mmoles) of 2,6-dimethyl-aniline for 3 hours at 140°-145° C. under nitrogen atmosphere with stirring. The mixture is cooled, dissolved in 40 ml of a 10% aqueous hydrochloric acid solution, and the solution is rendered alkaline (pH=9) with concentrated aqueous ammonia. The alkaline mixture is extracted thrice with 30 ml of chloroform, each. The chloroform solutions are combined, washed thrice with 30 ml of water, each, dried over magnesium sulfate, and the solvent is evaporated. The oily residue is distilled under reduced pressure. First the excess of 2,6-dimethyl-aniline is recovered (4.6 g, 98% of the excess; b.p.: 52°-62° C./53.3 Pa), and then the crude 1-(N-ethyl-acetamido)-2-(2,6-dimethylphenyl-amino)-propane distils at 120°-140° C./53.3 Pa. The resulting crude product, weighing 1.9 g (21%), is purified by chromatography on 80 g of silica gel; a 1:2 mixture of benzene and ethyl acetate is applied as eluant. A pure product, melting at 58°-60° C., is obtained. for 3 hours The mixture is cooled The alkaline mixture is extracted thrice with 30 ml of chloroform washed thrice with 30 ml of water each, dried over magnesium sulfate the solvent is evaporated The oily residue is distilled under reduced pressure First the excess of 2,6-dimethyl-aniline is recovered (4.6 g, 98% of the excess b.p.: 52°-62° C./53.3 Pa), and then the crude 1-(N-ethyl-acetamido)-2-(2,6-dimethylphenyl-amino)-propane distils at 120°-140° C./53.3 Pa is purified by chromatography on 80 g of silica gel a 1:2 mixture of benzene and ethyl acetate A pure product, melting at 58°-60° C., is obtained

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution comprising 480 mg 7-chloro-3-methyl-4-oxo-4H-pyridazino[6,1-c][1,2,4]triazine and 510 mg ethyl-(2-hydroxypropyl)amine in 10 ml toluene is heated to reflux for two hours, toluene is removed by evaporation, the remaining part if taken up with acetone, filtered, and the filtrate concentrated to a small volume. After cooling, 400 mg 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1, 2,4]triazine are collected under a vacuum, which melts at 140°-145° C. 1.3 grams 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1,2,4]triazine and 1 gram 2,4-dinitrophenylhydrazine are heated, while stirring, to 60° C. for three hours in 60 ml of 15% hydrochloric acid. These are cooled to 0° C. overnight, collected under a vacuum and washed with cold water. The mother liquors, after filtering, are evaporated to a dry condition, the residue being taken up twice with n.butylic alcohol and each time re-evaporated. A solid product is obtained which is triturated with 10 ml n.butylic alcohol, cooled, and collected under vacuum to yield 1 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting (with decomposition) at 212° C. is heated to reflux for two hours toluene is removed by evaporation filtered the filtrate concentrated to a small volume After cooling 400 mg 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1, 2,4]triazine are collected under a vacuum, which melts at 140°-145° C 1.3 grams 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1,2,4]triazine and 1 gram 2,4-dinitrophenylhydrazine are heated These are cooled to 0° C. overnight collected under a vacuum washed with cold water The mother liquors, after filtering are evaporated to a dry condition each time re-evaporated A solid product is obtained which is triturated with 10 ml n.butylic alcohol cooled collected under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 50% suspension of 1.5 g sodium hydride in 100 ml tetrahydrofuran, 3 g ethyl-(2-hydroxypropyl)amine are added; this is stirred at room temperature for 30 minutes, thereafter 4.5 g of 3-chloro-6-triphenylmethylazopyridazine are added. Stirring is maintained for 5 minutes, the organic phase is washed with a saturated solution of sodium chloride, rendered anhydrous and evaporated to dryness under a vacuum. The residue is taken up with ethyl alcohol, diluted with water, and the precipitate is collected under a vacuum which is then triturated with diisopropyl ether to yield 4 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine melting at 137° C. (with decomposition). A solution of 3 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine in 300 ml ethyl alcohol and 50 ml tetrahydrofuran containing 300 mg 5% palladium on carbon is hydrogenated at room temperature and pressure. The catalyst is filtered out, then the residue is evaporated and triturated with diethyl ether to yield 2.5 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine melting at 122° C. (with decomposition). A solution of 2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine in 100 ml absolute ethyl alcohol is mixed with 2.5 ml concentrated hydrochloric acid and stirred for 15 minutes at room temperature. This is evaporated under a vacuum and the residue taken up with isopropyl alcohol. This is diluted with diisopropyl ether to yield 1.2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting at 208°-212° C. (with decomposition). Stirring is maintained for 5 minutes the organic phase is washed with a saturated solution of sodium chloride evaporated to dryness under a vacuum diluted with water the precipitate is collected under a vacuum which is then triturated with diisopropyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 50% suspension of 1.5 g sodium hydride in 100 ml tetrahydrofuran, 3 g ethyl-(2-hydroxypropyl)amine are added; this is stirred at room temperature for 30 minutes, thereafter 4.5 g of 3-chloro-6-triphenylmethylazopyridazine are added. Stirring is maintained for 5 minutes, the organic phase is washed with a saturated solution of sodium chloride, rendered anhydrous and evaporated to dryness under a vacuum. The residue is taken up with ethyl alcohol, diluted with water, and the precipitate is collected under a vacuum which is then triturated with diisopropyl ether to yield 4 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine melting at 137° C. (with decomposition). A solution of 3 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine in 300 ml ethyl alcohol and 50 ml tetrahydrofuran containing 300 mg 5% palladium on carbon is hydrogenated at room temperature and pressure. The catalyst is filtered out, then the residue is evaporated and triturated with diethyl ether to yield 2.5 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine melting at 122° C. (with decomposition). A solution of 2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine in 100 ml absolute ethyl alcohol is mixed with 2.5 ml concentrated hydrochloric acid and stirred for 15 minutes at room temperature. This is evaporated under a vacuum and the residue taken up with isopropyl alcohol. This is diluted with diisopropyl ether to yield 1.2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting at 208°-212° C. (with decomposition). Stirring is maintained for 5 minutes the organic phase is washed with a saturated solution of sodium chloride evaporated to dryness under a vacuum diluted with water the precipitate is collected under a vacuum which is then triturated with diisopropyl ether