Dimethylformamide → 1-Ethyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amine

HRID 1731938Notes

Reaction equation

HRID 1731938 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:12]([CH2:15][CH3:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C[N:18](C)C=O>>[NH2:18][C:2]1[C:3]2[N:4]([C:12]([CH2:15][CH3:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 133857064-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 133857111-Ethyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amineYield 22%

Conditions

Temperature
0 °C

Procedure

Ammonia gas was bubbled through a solution of 1.2 g. (0.005 mole) of 4-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline (the product of Example 4) in N,N-dimethylformamide (20 ml.) at 0° C. for about 2 minutes. The solution was stirred at 0° C. for 30 minutes and at room temperature for one hour. The reaction mixture was then poured over ice and stirred for 20 minutes. The precipitate which formed was removed by filtration, washed with water and air dried. Recrystallization from ethanol afforded 220 mg. (22% yield) of pure 4-amino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 284°-8° C. Mass spectrum: m/e, 213 (P).

Workup

  1. customAmmonia gas was bubbled through a solution of 1.2 g
  2. additionThe reaction mixture was then poured over ice
  3. stirringstirred for 20 minutes
  4. customThe precipitate which formed
  5. customwas removed by filtration
  6. washwashed with water and air
  7. customdried
  8. customRecrystallization from ethanol
  9. customafforded 220 mg

Sources & evidence

ORD record
ord-d56a7d1adac940c39727e124dec8719b
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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