Toluene → HCID 22493536, compound

HRID 1596551Notes

Reaction equation

HRID 1596551 reaction equation
CC1C(C)=C(C=O)C(C)=C2[C:10]=1[NH:9][CH2:8][CH2:7]2.C([C:17]1[C:23](=O)[C:22](Cl)=[C:21](Cl)[C:19](=O)[C:18]=1[C:27]#N)#N.[C:29]1(C)C=CC=CC=1.[O:36]1CCOC[CH2:37]1>>[CH3:10][N:9]1[C:17]2[C:18](=[CH:19][C:21]([CH:37]=[O:36])=[CH:22][CH:23]=2)[C:27]([CH3:29])=[C:8]1[CH3:7]

Participants

5

Reactant 4

HCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 131722855HCID 131722855, compound

Product 1

HCID 22493536HCID 22493536, compound

Procedure

1,2,3-Trimethylindoline (21.5 g) was formulated 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-3404dbe2f48446178f73d0d485c7537e
Source dataset
uspto-grants-2001_09
Patent number
US06291508B1

Reaction notes

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