Ethyl orthopropionate → 4-Chloro-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 464301Notes

Reaction equation

HRID 464301 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][NH2:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[C:16](OCC)(OCC)(OCC)[CH2:17][CH3:18]>>[Cl:1][C:2]1[C:11]2[N:10]([C:16]([CH2:17][CH3:18])=[N:13][N:12]=2)[C:9]2[C:4]([N:3]=1)=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2

Participants

3

Reactant 2

HCID 66995Ethyl orthopropionateHCID 133856792-Chloro-3-hydrazino-6-methoxyquinoxaline

Product 1

HCID 133857264-Chloro-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxalineYield 35%

Procedure

2-Chloro-3-hydrazino-6-methoxyquinoxaline (1.3 g., 0.0058 mole) and 25 ml. of triethyl orthopropionate were heated at 100° C. for 4 hours and stirred at room temperature for 60 hours. The precipitate was removed by filtration and washed with ethanol. Recrystallization from ethanol then afforded 530 mg. (35% yield) of pure 4-chloro-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 196°-198° C. (decomp.).

Workup

  1. customThe precipitate was removed by filtration
  2. washwashed with ethanol
  3. customRecrystallization from ethanol
  4. customthen afforded 530 mg

Sources & evidence

ORD record
ord-528d91299091413597876dda39cb7343
Source dataset
uspto-grants-1985_10
Patent number
US04547501

Reaction notes

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