Toluene → HCID 22493536, compound

HRID 1601001Notes

Reaction equation

HRID 1601001 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[CH:4]([CH3:13])[CH:3]1[CH3:14].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C1(C)C=CC=CC=1>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[C:4]([CH3:13])=[C:3]1[CH3:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18466837HCID 18466837, compound

Product 1

HCID 22493536HCID 22493536, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,2,3-Trimethylindoline (21.5 g) was formylated in a similar manner to that described in Step 2 of Example 1 to obtain 20.1 g of 1,2,3-trimethylindoline-5-carbaldehyde. The obtained aldehyde (7.5 g) was dissolved in 200 ml of 1,4-dioxane, followed by the addition of 18 g of DDQ. The obtained mixture was heated under reflux for 2.5 hours, followed by the addition of 100 ml of toluene. Insolubles were filtered out and the organic phase was concentrated in a vacuum. The obtained residue was purified by flash column chromatography to give 900 mg of the title compound.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. filtrationInsolubles were filtered out
  4. concentrationthe organic phase was concentrated in a vacuum
  5. customThe obtained residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-685ce73ec6f8414c9e94df4d131064be
Source dataset
uspto-grants-1999_11
Patent number
US05977125

Reaction notes

Loading…