Trimethylorthoacetate → 6-Bromo-3-methyl-8-nitro-[1,2,4]triazolo[4,3-a]pyridine

HRID 2205721Notes

Reaction equation

HRID 2205721 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH3:13][C:14](C)(C)C([O-])([O-])[O-]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]2[N:6]([C:13]([CH3:14])=[N:9][N:8]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 21927715TrimethylorthoacetateHCID 263702005-Bromo-2-hydrazinyl-3-nitropyridine

Product 1

HCID 581189676-Bromo-3-methyl-8-nitro-[1,2,4]triazolo[4,3-a]pyridine

Conditions

Temperature
80 °C

Procedure

A suspension of 5-bromo-3-nitro-2-hydrazinopyridine (2.0 g, 8.58 mmol) in trimethylorthoacetate (20 mL) was heated at 80° C. for 20 h. After cooling, the solvent was distilled off, the residue was dissolved in ethyl acetate (200 mL), washed with water, brine, dried over sodium sulphate and concentrated to provide the product 6-bromo-3-methyl-8-nitro-[1,2,4]triazolo[4,3-a]pyridine.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f312f9259f004748b279a8779cb13d7e
Source dataset
uspto-grants-2016_06
Patent number
US09371329B2

Reaction notes

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