Toluene → 9-Ethyl-5-ethoxycarbazole-6-carboxylic acid

HRID 50612Notes

Reaction equation

HRID 50612 reaction equation
C(O[C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[NH:14]2)=[CH:6][C:5]=1[C:17]([OH:19])=[O:18])C.C1(Cl)C(=O)C(Cl)=C(Cl)[C:22](=[O:23])[C:21]=1Cl.[C:32]1(C)C=CC=C[CH:33]=1>>[CH2:32]([N:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[C:15]1=[CH:16][CH:4]=[C:5]([C:17]([OH:19])=[O:18])[C:6]=2[O:23][CH2:22][CH3:21])[CH3:33]

Participants

4

Reactant 3

HCID 1140TolueneHCID 8371ChloranilHCID 698875637-Ethoxytetrahydrocarbazole-6-carboxylic acid

Product 1

HCID 227361469-Ethyl-5-ethoxycarbazole-6-carboxylic acid

Procedure

The 7-ethoxytetrahydrocarbazole-6-carboxylic acid obtained in Example 37 was dissolved in 8 mL of toluene, and the solution was added with 2.14 g of chloranil and refluxed for 2 hours and 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (ethyl acetate) to obtain 336 mg of 9-ethyl-5-ethoxycarbazole-6-carboxylic acid. Compound 1-38 was obtained in the same manner as in Example 36 except that the 9-ethyl-5-ethoxycarbazole-6-carboxylic acid obtained was used.

Workup

  1. temperaturerefluxed for 2 hours and 30 minutes
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bf84dbc72e724a1cb63717346ff96827
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Reaction notes

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