Methanol → HCID 22614878, compound

HRID 343800Notes

Reaction equation

HRID 343800 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][OH:5].NC1C(C)=C(Cl)C=C2C=1N=C(Cl)C(Cl)=N2.[NH2:21][C:22]1[C:31]([Cl:32])=[C:30]([CH3:33])[CH:29]=[C:28]2[C:23]=1[N:24]=[C:25](Cl)[C:26](Cl)=[N:27]2>O1CCCC1.C(OCC)(=O)C>[NH2:21][C:22]1[C:31]([Cl:32])=[C:30]([CH3:33])[CH:29]=[C:28]2[C:23]=1[N:24]=[C:25]([O:5][CH3:4])[C:26]([O:2][CH3:1])=[N:27]2

Participants

7

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 22614838HCID 22614838, compoundHCID 22614843HCID 22614843, compound

Product 1

HCID 22614878HCID 22614878, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 25% solution of sodium methoxide in methanol (433 μl, 1.89 mmol) was added dropwise to a solution of 5-amino-2,3,7-trichloro-6-methylquinoxaline and 5-amino-2,3,6-trichloro-7-methylquinoxaline (200 mg, 0.788 mmol) in dry tetrahydrofuran (7.9 ml) at 0° C. under nitrogen. The mixture was stirred for 31/4 hours and then diluted with ethyl acetate (30 ml) and washed with water (2×10 ml) and brine (10 ml) and then dried (MgSO4) filtered and concentrated under reduced pressure. The solid residue was purified by flash chromatography on silica gel, eluting with a hexane/ethyl acetate gradient giving 5-amino-6-chloro-2,3-dimethoxy-7-methylquinoxaline as an off-white solid, mp 169°-170° C.

Workup

  1. washwashed with water (2×10 ml) and brine (10 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe solid residue was purified by flash chromatography on silica gel
  6. washeluting with a hexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-96d4f10842fb46da80b5b484689b9540
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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