Hydrochloric Acid → 3-Pyridinecarbonyl Azide

HRID 1904689Notes

Reaction equation

HRID 1904689 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Cl.[N:12]([O-])=O.[Na+]>>[C:1]([N:9]=[N+:10]=[N-:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11112Nicotinic acid, hydrazideHCID 23668193Sodium Nitrite

Product 1

HCID 199143-Pyridinecarbonyl AzideYield 82.3%

Conditions

Temperature
0 °C

Procedure

Nicotinic acid hydrazide (18 g) was added in small portions with ice cooling to 22 ml concentrated hydrochloric acid, and 30 ml of aqueous solution of 18 g sodium nitrite was then added dropwise while maintaining the temperature at 0° C. or lower. The mixture was stirred at 0° C. for 15 minutes and extracted with ether, the extract was washed with an aqueous solution of sodium bicarbonate and dried over anhydrous sodium sulfate, and the solvent was distilled off from the dried solution, giving 16 g of nicotinic acid azide.

Workup

  1. additionwas then added dropwise
  2. extractionextracted with ether
  3. washthe extract was washed with an aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off from the dried solution

Sources & evidence

ORD record
ord-9a8cc0a5fb1a4e689d128215c11e322b
Source dataset
uspto-grants-1989_06
Patent number
US04839376

Reaction notes

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