3-Methoxybenzene-1,2-diamine → 5-Methoxyquinoxaline

HRID 275788

Reaction equation

HRID 275788 reaction equation
O.S(=O)(O)[O-].[Na+].[CH:7]([CH:9]=O)=O.[NH2:11][C:12]1[C:17]([NH2:18])=[CH:16][CH:15]=[CH:14][C:13]=1[O:19][CH3:20]>O.C(O)C.Cl>[CH3:20][O:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[N:11]=[CH:7][CH:9]=[N:18]2

Participants

6

Reactant 2

HCID 1842683-Methoxybenzene-1,2-diamineHCID 23685989Glyoxal-sodium bisulfite hydrate

Product 1

HCID 132383925-MethoxyquinoxalineYield 77.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Glyoxal sodium bisulphite hydrate (10.0 g) in water (80 ml) was warmed to 60° C. then a solution of 2,3-diaminoanisole (3.40 g) in ethanol (40 ml) was added. The stirred mixture was then heated to 80° C. for 1 h before addition of concentrated hydrochloric acid (6 drops). Heating was continued for 1 h. It was allowed to cool overnight, concentrated in vacuo and poured into aqueous potassium carbonate (40 ml). Ethyl acetate (3×100 ml) extracts were washed with water (100 ml) and saturated brine (50 ml) then dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo to afford the title compound as a yellow solid (3.07 g).

Workup

  1. temperatureHeating
  2. temperatureto cool overnight
  3. concentrationconcentrated in vacuo
  4. additionpoured into aqueous potassium carbonate (40 ml)
  5. washEthyl acetate (3×100 ml) extracts were washed with water (100 ml) and saturated brine (50 ml)
  6. dry with materialthen dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a693d42e681d4e4b8ec4f4f16a2ddd56
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Linked notes

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