Hydrochloric Acid → Pyridine, 2-azido-5-chloro-, 1-oxide

Temperature

25 °C

In this example, 6.70 grams (0.036 mol) of 2-amino-5-chloropyridine N-oxide hydrochloride was added to and dissolved in 100 ml. of water and 10 ml. of concentrated hydrochloric acid under vigorous stirring and was thus cooled to 0° C. to 5° C. in a salt-ice bath. To the above cold solution, a solution of 2.50 grams (0.036 mol) in 30 ml. of water was added dropwise at such a rate that the temperature of the reaction mixture did not rise above 5° C. Immediately after the above addition was complete a solution of 2.30 grams (0.036 mol) of sodium azide in 30 ml. of water was added to the cold vigorously stirred above solution at such a rate that the temperature did not rise above 5° C. When the above addition was complete the cooling bath was removed and the solution slowly warmed to about 25° C. The reaction mixture was continuously extracted with methylene chloride. From the methylene chloride extract, after evaporation in vacuo was obtained 2-azido-5-chloropyridine N-oxide in a yield of 3.75 grams or 62% of theory having a melting point of 80° C. to 82° C. with decomposition.

1. dissolutiondissolved in 100 ml
2. temperaturewas thus cooled to 0° C. to 5° C. in a salt-ice bath
3. customdid not rise above 5° C
4. additionImmediately after the above addition
5. customdid not rise above 5° C
6. additionWhen the above addition
7. customwas removed
8. extractionThe reaction mixture was continuously extracted with methylene chloride
9. extractionFrom the methylene chloride extract
10. customafter evaporation in vacuo

ORD record

ord-1918c61ee4af41638308ff1aa51e44d9

Source dataset

uspto-grants-1977_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04006160