Ammonium Chloride → 6,7-Dichloro-2,3-dimethoxy-5-(1-hydroxyethyl)quinoxaline

HRID 1957124Notes

Reaction equation

HRID 1957124 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[C:6]([CH:20]=[O:21])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11]=[C:10]([O:16][CH3:17])[C:9]([O:18][CH3:19])=[N:8]2.[Cl-].[NH4+]>O1CCCC1>[Cl:4][C:5]1[C:6]([CH:20]([OH:21])[CH3:1])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11]=[C:10]([O:16][CH3:17])[C:9]([O:18][CH3:19])=[N:8]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 104934926,7-Dichloro-2,3-dimethoxy-5-formylquinoxalineHCID 178418573HCID 178418573, compound

Product 1

HCID 190688846,7-Dichloro-2,3-dimethoxy-5-(1-hydroxyethyl)quinoxalineYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (2.3 mL, 1M in di-n-butylether, 2.3 mmol) was added to a suspension of 6,7-dichloro-2,3-dimethoxy-5-formylquinoxaline (600 mg, 2.09 mmol) in dry tetrahydrofuran (30 mL) under nitrogen at room temperature. After 30 minutes, saturated ammonium chloride (20 mL) was added, and the product was extracted into ethyl acetate (2×30 mL). The combined extracts were dried (MgSO4) and concentrated under reduced pressure to give 6,7-dichloro-2,3-dimethoxy-5-(1-hydroxyethyl)quinoxaline (577 mg, 91%), as a creamy coloured solid.

Workup

  1. extractionthe product was extracted into ethyl acetate (2×30 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-967ebc73364e491b8612c8b206a237e6
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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