Ammonia → 2-Amino-6,7-dichloro-3-ethoxy-quinoxaline

HRID 1578073Notes

Reaction equation

HRID 1578073 reaction equation
Cl[C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[NH3:15].[CH2:16]([OH:18])[CH3:17]>>[NH2:15][C:2]1[C:11]([O:18][CH2:16][CH3:17])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 40971682,3,6,7-Tetrachloroquinoxaline

Product 1

HCID 140675342-Amino-6,7-dichloro-3-ethoxy-quinoxaline

Conditions

Temperature
80 °C

Procedure

A solution of 3.46 g of 2,3,6,7-tetrachloroquinoxaline in 200 ml of ethanol was saturated with ammonia at 0° C. and was then shaken overnight at 80° C. under pressure in a Cook Hydrogenator. The solution was evaporated to dryness and the residue was triturated with water to obtain a buff crystalline solid. The latter was chromatographed over silica gel and was eluted with a 1-1 ethyl acetate-petroleum ether (b.p.=60° to 80° C.) mixture to obtain 1.36 g of 2-amino-6,7-dichloro-3-ethoxy-quinoxaline melting at 191°-193° C.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was triturated with water
  3. customto obtain a buff crystalline solid
  4. customThe latter was chromatographed over silica gel
  5. washwas eluted with a 1-1 ethyl acetate-petroleum ether (b.p.=60° to 80° C.) mixture

Sources & evidence

ORD record
ord-184b8f04d2cc47ebb3d6535e17a3256d
Source dataset
uspto-grants-1981_09
Patent number
US04291033

Reaction notes

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