Methylamine → 4-Methylamino-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 464284Notes

Reaction equation

HRID 464284 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:12]=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:15][NH2:16]>CN(C)C=O>[CH3:15][NH:16][C:2]1[C:3]2[N:4]([CH:12]=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 11261184-Chloro[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 133856804-Methylamino-[1,2,4]triazolo[4,3-a]quinoxalineYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-[1,2,4]triazolo-[4,3-a]quinoxaline (2.0 g., 0.01 mole), the product of Example 2, in N,N-dimethyl formamide (30 ml.) was saturated with monomethylamine gas and stirred at room temperature for 3 hours. Monomethylamine gas was again bubbled into the solution and the solution was stirred at room temperature for an additional 2 hours. The precipitate was separated by filtration and washed with N,N-dimethylformamide. Recrystallization from N,N-dimethylformamide gave 1.37 g. (69% yield) of 4-methylamino-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. >300° C. Mass spectrum: m/e, 199 (P).

Workup

  1. customMonomethylamine gas was again bubbled into the solution
  2. stirringthe solution was stirred at room temperature for an additional 2 hours
  3. customThe precipitate was separated by filtration
  4. washwashed with N,N-dimethylformamide
  5. customRecrystallization from N,N-dimethylformamide
  6. customgave 1.37 g

Sources & evidence

ORD record
ord-2dff22469f354642a4f50a84a904df53
Source dataset
uspto-grants-1985_10
Patent number
US04547501

Reaction notes

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