Water → HCID 53823228, compound

HRID 597053Notes

Reaction equation

HRID 597053 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]([CH3:17])[CH:11]2[CH2:18][C:19]([O:21][CH3:22])=[O:20].[Cl:23][C:24]1[C:33](Cl)=[N:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1.O>COCCOCCOC>[Cl:23][C:24]1[C:33]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([O:7][CH3:6])=[CH:16][CH:15]=3)[CH:11]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:12]2[CH3:17])=[N:32][C:31]2[C:26]([N:25]=1)=[CH:27][CH:28]=[CH:29][CH:30]=2

Participants

6

Reactant 4

HCID 962WaterHCID 166592,3-DichloroquinoxalineHCID 517045Sodium AcetateHCID 21449392HCID 21449392, compound

Product 1

HCID 53823228HCID 53823228, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Anhydrous sodium acetate (3.6 g.) was added to a mixture of methyl 5-methoxy-2-methylindolin-3-ylacetate (8.0 g.) and 2,3-dichloroquinoxaline (6.8 g.) in diethyleneglycol dimethyl ether (150 ml.), and the mixture was heated under reflux for 12 hrs. The mixture was then cooled and poured into water (800 ml.), and the aqueous suspension was extracted with ethyl acetate (3 × 50 ml.). The combined extracts were washed successively with water (4 × 30 ml.) and a saturated aqueous solution of sodium chloride (50 ml.), and then dried (MgSO4) and evaporated. The resultant syrup was chromatographed on chromatographic silica gel (M.F.C., 300 g.) using an increasing gradient of diethyl ether in petroleum ether (b.p. 40°-60° C.) (polarity increased by incremental addition of 10% v/v ether.) The combined eluate was evaporated to give methyl 1-(3-chloroquinoxalin-2-yl)-5-methoxy-2-methylindolin-3-ylacetate, m.p. 155°-157° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hrs
  3. temperatureThe mixture was then cooled
  4. extractionthe aqueous suspension was extracted with ethyl acetate (3 × 50 ml.)
  5. washThe combined extracts were washed successively with water (4 × 30 ml.)
  6. dry with materiala saturated aqueous solution of sodium chloride (50 ml.), and then dried (MgSO4)
  7. customevaporated
  8. customThe resultant syrup was chromatographed on chromatographic silica gel (M.F.C., 300 g.)
  9. temperatureincreased by incremental addition of 10% v/v ether
  10. custom) The combined eluate was evaporated

Sources & evidence

ORD record
ord-eca0d0792b914cc78acf748a51eb9e66
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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