Acetic Acid → 8-Bromo-1-methyl-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 711384Notes

Reaction equation

HRID 711384 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH2:13])=[N:9]2)=[CH:4][CH:3]=1.[C:14](O)(=O)[CH3:15]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]3[N:9]2[C:14]([CH3:15])=[N:13][N:12]=3)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 52002657-Bromo-2-hydrazinylquinoxaline

Product 1

HCID 668035548-Bromo-1-methyl-[1,2,4]triazolo[4,3-a]quinoxalineYield 90%

Procedure

A mixture of 7-bromo-2-hydrazinylquinoxaline (1 g, 4.18 mmol) in acetic acid (10 mL) was refluxed for 18 h. Half of the acetic acid was removed under vacuum and the residue was poured into ice-water. The precipitate was collected on a filter, washed with water, and dried under vacuo to afford crude 8-bromo-1-methyl-[1,2,4]triazolo[4,3-a]quinoxaline as a dark red solid (1 g, yield 90%) which was used in the next step without further purification. MS (m/z): 263 (M+H)+.

Workup

  1. temperaturewas refluxed for 18 h
  2. customHalf of the acetic acid was removed under vacuum
  3. additionthe residue was poured into ice-water
  4. customThe precipitate was collected on a filter
  5. washwashed with water
  6. customdried under vacuo

Sources & evidence

ORD record
ord-5d14d82332fb4e68aafe04a1a681c519
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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