Methanol → HCID 53999444, compound

HRID 343811Notes

Reaction equation

HRID 343811 reaction equation
NC1C(CC)=C(Cl)C=C2C=1N=C(Cl)C(Cl)=N2.[NH2:17][C:18]1[C:27]([Cl:28])=[C:26]([CH2:29][CH3:30])[CH:25]=[C:24]2[C:19]=1[N:20]=[C:21](Cl)[C:22](Cl)=[N:23]2.[CH3:33][O-:34].[Na+].[CH3:36][OH:37]>O1CCCC1.C(OCC)(=O)C>[NH2:17][C:18]1[C:27]([Cl:28])=[C:26]([CH2:29][CH3:30])[CH:25]=[C:24]2[C:19]=1[N:20]=[C:21]([O:37][CH3:36])[C:22]([O:34][CH3:33])=[N:23]2

Participants

7

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 54395338HCID 54395338, compoundHCID 54482221HCID 54482221, compound

Product 1

HCID 53999444HCID 53999444, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-amino-2,3,7-trichloro6-ethylquinoxaline and 5-amino-2,3,6-trichloro-7-ethylquinoxaline (169 mg, 0.611 mmol) in anhydrous tetrahydrofuran (6 ml) was treated with a 25% solution of sodium methoxide in methanol (0.84 ml, 1.47 mmol) at 0° C. with stirring. After 3.5 hours, the solution was diluted with ethyl acetate, washed with water (2×10 ml), saturated aqueous sodium chloride (10 ml), dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (eluting with hexane/ethyl acetate 19:1) gave two products. The first eluted compound, 5-amino-6-chloro-7-ethyl-2,3-dimethoxyquinoxaline (42 mg, 26%), was obtained as a white solid.

Workup

  1. washwashed with water (2×10 ml), saturated aqueous sodium chloride (10 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washby flash chromatography (eluting with hexane/ethyl acetate 19:1)
  6. customgave two products

Sources & evidence

ORD record
ord-febc942395d7428da86095ca9c86a7e7
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

Loading…