Methanol → HCID 22614878, compound

HRID 842690Notes

Reaction equation

HRID 842690 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, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 25% w/w solution of sodium methoxide in methanol (433 μL, 1.89 mmol) was added dropwise to a solution of the above mixture 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 3 hours, diluted with ethyl acetate (30 mL), washed with water (2×10 mL), brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The solid residue was purified by flash chromatography on silica gel, by gradient elution using hexane:ethyl acetate (95:5 changing to 1:1, by volume) to give as the first eluted isomer, 5-amino-6-chloro-2,3-dimethoxy-7-methylquinoxaline (48 mg, 25%) as an off-white solid, mp 169-170° C.

Workup

  1. washwashed with water (2×10 mL), 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, by gradient elution

Sources & evidence

ORD record
ord-1417d63ae503481cba44122ead2b0521
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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