Dimethylformamide → 9-Phenyl-9H-carbazole-3-carbaldehyde

HRID 1369369Notes

Reaction equation

HRID 1369369 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.CN([CH:28]=[O:29])C>ClC(Cl)C.Cl>[C:1]1([N:7]2[C:8]3[CH:9]=[CH:10][C:11]([CH:28]=[O:29])=[CH:12][C:13]=3[C:14]3[C:19]2=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 708519-Phenylcarbazole

Product 1

HCID 185154409-Phenyl-9H-carbazole-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 0.49 g of N-phenylcarbazole in 2 mL of dichloroethane is added 0.19 mL of phosphorus oxychloride and 0.5 mL of DMF. The resulting mixture is stirred at 40° C. overnight. After stirring, 1 mL of 1 M HCl is added. After 5 additional minutes, the mixture is diluted with 1 M HCl and extracted with ethyl acetate. The crude product is purified by column chromatography on silica gel to give 60 mg of Compound 7.

Workup

  1. stirringAfter stirring
  2. extractionextracted with ethyl acetate
  3. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4cca24318bbc4925bc21d2465003b4e1
Source dataset
uspto-grants-2003_06
Patent number
US06579718B1

Reaction notes

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