HCID 43811255, compound → Ethyl 6-methoxy-9H-carbazole-3-carboxylate

HRID 348518Notes

Reaction equation

HRID 348518 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[NH:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CC1C=CC(C(C)C)=CC=1.ClCCl.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 43811255HCID 43811255, compound

Product 1

HCID 66720295Ethyl 6-methoxy-9H-carbazole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 7463P-CymeneSolvent

Conditions

Temperature
190 °C

Procedure

A solution of 6-methoxy-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid ethyl ester (3.29 g, 12.1 mmol) in p-cymene (12 mL) was treated with palladium (10% on carbon, 2.25 g) and heated at 190° C. for 20 hours. The mixture was then cooled, diluted with dichloromethane and filtered over a pad of diatomaceous earth. The filtrate was concentrated in vacuo to a low volume and heptane (200 mL) was added to precipitate the title compound as a white solid (2.78 g).

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered over a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated in vacuo to a low volume and heptane (200 mL)
  4. additionwas added
  5. customto precipitate the title compound as a white solid (2.78 g)

Sources & evidence

ORD record
ord-0dd29d21a3e34c908df95b11055674a6
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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