Hydrochloric Acid → 3-Pyridinecarbonyl Azide

HRID 981179Notes

Reaction equation

HRID 981179 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-f26a9fe1e63c4d0c97e8bc1f60d8ac0d
Source dataset
uspto-grants-1991_02
Patent number
US04990529

Reaction notes

Loading…