o-Chloranil → HCID 67300410, compound

HRID 1015443Notes

Reaction equation

HRID 1015443 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=2)[CH:10]([CH3:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl>COC(C)(C)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH3:21])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 73252o-ChloranilHCID 57608623HCID 57608623, compound

Product 1

HCID 67300410HCID 67300410, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A 269 mg portion of methyl 1-benzyl-3-methylindoline-5-carboxylate was dissolved in 10 ml of tert-butyl methyl ether, and 235 mg of o-chloranil was added, followed by stirring at room temperature for 1 hour. After dilution with ethyl acetate and subsequent washing with a 1 M sodium hydroxide aqueous solution, it was dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:20 to 1:10) to obtain 433 mg of methyl 1-benzyl-3-methyl-1H-indole-5-carboxylate as a colorless solid.

Workup

  1. washAfter dilution with ethyl acetate and subsequent washing with a 1 M sodium hydroxide aqueous solution, it
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:20 to 1:10)

Sources & evidence

ORD record
ord-b6b02395fd384f879597907ceab9f61f
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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