Toluene → 9-Benzylcarbazole-3,6-dicarboxaldehyde

HRID 1597735Notes

Reaction equation

HRID 1597735 reaction equation
C1(C)C=CC([N:7]2[C:19]3[CH:18]=[CH:17]C=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=CC=1.CN([CH:24]=[O:25])C.P(Cl)(Cl)(Cl)=O.[C:31]1([CH3:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O:41][CH2:42][CH3:43])(=O)C>[Cl-].[Zn+2].[Cl-]>[CH:24]([C:11]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][C:43]([CH:42]=[O:41])=[CH:17][CH:18]=3)=[O:25]

Participants

7

Reactant 5

HCID 1140Toluene2×HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 157986519-(p-Tolyl)carbazole

Product 1

HCID 189318919-Benzylcarbazole-3,6-dicarboxaldehydeYield 23.5%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

7.0 g (27.2 mmol) of 9-benzylcarbazole (4d), 11.8 g (161.4 mmol) of DMF, 4.0 g (29.3 mmol) of zinc chloride, 17.0 g (110.9 mmol) of phosphorus oxychloride and 100 ml of toluene were allowed to react and after treated in the same manner as with Example 1 (1), and treated by silica gel column chromatography (eluent: toluene, and then ethyl acetate) to obtain crystals. These crystals were recrystallized from ethyl acetate toluene to obtain 3.0 g of 3,6-diformyl-9-benzylcarbazole.

Workup

  1. customto react
  2. additiontreated by silica gel column chromatography (eluent
  3. customThese crystals were recrystallized from ethyl acetate toluene

Sources & evidence

ORD record
ord-75b66c9dbd0943d09fa4a8e4f9c55ed0
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

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