Sodium Chloride → 6,7-Dichloro-2,3-dimethoxy-5-(1-hydroxypropyl)-quinoxaline

HRID 1957130Notes

Reaction equation

HRID 1957130 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Cl:5][C:6]1[C:7]([CH:21]=[O:22])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2.[Cl-].[Na+]>O1CCCC1>[Cl:5][C:6]1[C:7]([CH:21]([OH:22])[CH2:1][CH3:2])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 104934926,7-Dichloro-2,3-dimethoxy-5-formylquinoxalineHCID 178418443HCID 178418443, compound

Product 1

HCID 108529296,7-Dichloro-2,3-dimethoxy-5-(1-hydroxypropyl)-quinoxalineYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (9.08 mL, 3M in diethyl ether) was added to a suspension of 6,7dichloro-2,3-dimethoxy-5-formylquinoxaline (3.91 g, 13.62 mmol) (Preparation 2) in dry tetrahydrofuran (200 mL) under nitrogen at room temperature. After 30 minutes, saturated sodium chloride (50 mL) was added, and the product was extracted into ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (eluting with dichloromethane) gave 6,7-dichloro-2,3-dimethoxy-5-(1-hydroxypropyl)-quinoxaline (1.86 g, 43%), as a pale yellow solid.

Workup

  1. extractionthe product was extracted into ethyl acetate (2×100 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washby flash chromatography (eluting with dichloromethane)

Sources & evidence

ORD record
ord-62fd8c3703064ac6b36a1fb7d70848bf
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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