反应详情

3.0 g of N-(2-hydroxyethyl)pyridine-2-carboxamide were placed in a round flask with 20 ml of methylene chloride and 2.5 ml of triethylamine and the mixture was cooled to 0°-5°. A solution of 1.4 ml of methanesulfochloride in 30 ml of methylene chloride was added dropwise thereto while cooling well at 0°-5°. The reaction mixture was stirred at 0°-5° for a further 2 hours and thereafter added dropwise at 0°-5° to 30 ml of concentrated (25%) ammonia. The reaction mixture was stirred at room temperature overnight and thereafter concentrated under reduced pressure. The residue was dissolved in methylene chloride, extracted with 2N hydrochloric acid and washed with water. The aqueous extracts were combined, made basic with concentrated (28%) sodium hydroxide solution and extracted 3 times with methylene chloride. The organic extracts were dried over magnesium sulfate, filtered and evaporated. There was obtained a yellow oil which was chromatographed on silica gel for further purification. As the elution agent there was used firstly ethyl acetate, thereafter an ethyl acetate/alcohol mixture and finally alcohol. There was obtained N-(2-aminoethyl)pyridine-2-carboxamide which, in accordance with thin-layer chromatography, was identical with the compound described in Example 1.

1. temperaturethe mixture was cooled to 0°-5°
2. temperaturewhile cooling well at 0°-5°
3. additionadded dropwise at 0°-5° to 30 ml
4. concentrationof concentrated (25%) ammonia
5. stirringThe reaction mixture was stirred at room temperature overnight
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in methylene chloride
8. extractionextracted with 2N hydrochloric acid
9. washwashed with water
10. concentrationwith concentrated (28%) sodium hydroxide solution
11. extractionextracted 3 times with methylene chloride
12. dry with materialThe organic extracts were dried over magnesium sulfate
13. filtrationfiltered
14. customevaporated
15. customThere was obtained a yellow oil which
16. customwas chromatographed on silica gel for further purification