2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Formyl-5-methoxy-3-methoxycarbonyl-1-methylindole

HRID 2225886Notes

Reaction equation

HRID 2225886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([CH2:13][O:14]C)=[C:6]2[C:16]([O:18][CH3:19])=[O:17].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH:13]([C:7]1[N:8]([CH3:12])[C:9]2[C:5]([C:6]=1[C:16]([O:18][CH3:19])=[O:17])=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)=[O:14]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 106591965-Methoxy-3-methoxycarbonyl-2-methoxymethyl-1-methylindole

Product 1

HCID 107529932-Formyl-5-methoxy-3-methoxycarbonyl-1-methylindoleYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.0 g (19.0 mmol) of 5-methoxy-3-methoxycarbonyl-2-methoxymethyl -1-methylindole obtained in Example 2 or 4 was dissolved in 200 ml of anhydrous toluene, followed by the addition of 4.94 g (20.9 mmol) of DDQ and subsequent 2 hours of heating under reflux. After cooling the reaction mixture and removing impurities by filtration, the organic layer was washed with water and saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off and the solvent was distilled off under reduced pressure, the resulting residue was purified by a silica gel column chromatography (eluent: hexaneethyl acetate, 3:1) to obtain 3.38 g of the title compound with a yield of 72%.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. temperatureAfter cooling the reaction mixture
  4. customremoving impurities
  5. filtrationby filtration
  6. washthe organic layer was washed with water and saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter anhydrous magnesium sulfate was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexaneethyl acetate, 3:1)

Sources & evidence

ORD record
ord-7e54d5054b094e548ab2d0465c096eb5
Source dataset
uspto-grants-1994_09
Patent number
US05344938

Reaction notes

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