Sulfuric Acid → 3-(6-Methylpyridin-2-yl)-3H-[1,2,3]triazolo[4,5-b]pyridine

HRID 1974325Notes

Reaction equation

HRID 1974325 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[N:14]=[C:13]([CH3:15])[CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[N:21]([O-])=O.[Na+]>O>[CH3:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([N:8]2[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[N:1]=[N:21]2)[N:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12445539HCID 12445539, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 124455483-(6-Methylpyridin-2-yl)-3H-[1,2,3]triazolo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1.0 g. of the crude amine from Step B, 20 ml. of water and 3 ml. of concentrated sulfuric acid was stirred, cooled to 0°-5° C. and treated dropwise with a solution of 0.345 g. of sodium nitrite in 2 ml. of water. After an additional hour at 0°-5° C. and storage at room temperature over the weekend, the precipitate was collected and recrystallized from 6 ml. of ethanol to give 3-(2-methyl-6-pyridyl)-3H-1,2,3-triazolo[4,5-b]pyridine, m.p. 144°-145° C.

Workup

  1. additionA mixture of 1.0 g
  2. temperaturecooled to 0°-5° C.
  3. additiontreated dropwise with a solution of 0.345 g
  4. waitAfter an additional hour at 0°-5° C.
  5. customstorage at room temperature over the weekend, the precipitate was collected
  6. customrecrystallized from 6 ml

Sources & evidence

ORD record
ord-cff836c7c84d42e386474d085f9e1ef2
Source dataset
uspto-grants-1976_12
Patent number
US04000286

Reaction notes

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