Hydrochloric Acid → 1-(Tetrazolo[1,5-a]pyridin-6-yl)ethan-1-one

HRID 1788916Notes

Reaction equation

HRID 1788916 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][N:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].C(O)C.Cl>O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]2[N:3]([N:11]=[N:12][N:13]=2)[CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 33557Sodium AzideHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 130903111-(Tetrazolo[1,5-a]pyridin-6-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 8.4 gm. (51.6 mmoles) of 2-chloro-5-acetylpyridine and 8.4 gm. (129 mmoles) of sodium azide in 150 ml. of ethanol and 150 ml. of water was added 75 ml. of 10% HCl over a period of 20min. The reaction mixture was then heated to reflux for 18 hours, cooled in an ice bath and the resulting crystals filtered off to give a first crop of 6.0 gm. A second crop of 1.0 gm. was obtained for a total of 7.0 gm. of A, (84.% yield), m.p. 159°-160° C.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 18 hours
  3. temperaturecooled in an ice bath
  4. filtrationthe resulting crystals filtered off
  5. customto give a first crop of 6.0 gm
  6. customwas obtained for a total of 7.0 gm

Sources & evidence

ORD record
ord-40f86100453649baaaad16821658abaf
Source dataset
uspto-grants-1987_08
Patent number
US04686222

Reaction notes

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