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

HRID 1846926Notes

Reaction equation

HRID 1846926 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-ae189dfbf11c4159acd2de9bdfff3ef4
Source dataset
uspto-grants-2015_02
Patent number
US08952034B2

Reaction notes

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