Methanol → HCID 22419799, compound

HRID 1720004Notes

Reaction equation

HRID 1720004 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:3]=1.[Na].[CH3:17][OH:18]>>[Cl:12][C:11]1[C:2]([O:18][CH3:17])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2

Participants

4

Reactant 3

HCID 887Methanol2×HCID 6890902,3-Dichloro-6-nitroquinoxalineHCID 5360545Sodium

Product 1

HCID 22419799HCID 22419799, compoundYield 58%

Conditions

Temperature
50 °C

Procedure

A slurry of 6.1 g (25 mmol) of 2,3-dichloro-6-nitroquinoxaline in 70 ml of dry methanol was heated to 50° C and treated dropwise over 5 h with 0.7 g (30 mmol) of sodium dissolved in 70 ml of dry methanol. The mixture was stirred over night at 50° C., cooled and filtered. The resulting precipitate was washed with cold ethanol and water and finally chromatographed on silica gel with toluene to give 3.5 g (58%) of the title compound; m.p. 155-158° C.; 1H-NMR (DMSO-d6): δ4.17 (s, 3H, CH3), 8.05 (d,J=9 Hz, 1H, H-8), 8.48 (dd, J7-8 =9 Hz, J7-5 =2 Hz, 1H, H-7), 8.73 (d, J=2 Hz, 1H, H-5).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe resulting precipitate was washed with cold ethanol and water
  4. customfinally chromatographed on silica gel with toluene

Sources & evidence

ORD record
ord-480e5021370148ca9f9bd7f4d2093bd4
Source dataset
uspto-grants-1996_04
Patent number
US05504085

Reaction notes

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