Hydrochloric Acid → 9H-Carbazole-3-carboxylic acid

HRID 50615Notes

Reaction equation

HRID 50615 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].[OH-].[Na+].Cl>CO>[CH:7]1[C:8]2[NH:9][C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[CH:17]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 504069Methyl Carbazole-3-Carboxylate

Product 1

HCID 31520239H-Carbazole-3-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Carbazole-3-carboxylic acid methyl ester (450 mg) was dissolved in 7 mL of methanol, and the solution was added with 2.5 mL of 2 N aqueous sodium hydroxide, and stirred at 60° C. for 3 hours. Subsequently, the reaction mixture was cooled and then neutralized with hydrochloric acid, and the deposited precipitates were collected to obtain 410 mg of carbazole-3-carboxylic acid. The resulting carbazole-3-carboxylic acid (205 mg), 6-(1-naphthalenesulfonyl)aminopentylamine (292 mg) obtained in the example and WSC (192 mg) were dissolved in 5 mL of DMF and stirred at room temperature for 3 hours. The reaction mixture was added with water and extracted with ethyl acetate. Then, the organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: chloroform/methanol=95/5) to obtain 123 mg of the compound, 3-(1-naphthylsulfonylaminopentylaminocarbonyl)carbazole.

Workup

  1. temperatureSubsequently, the reaction mixture was cooled
  2. customthe deposited precipitates
  3. customwere collected

Sources & evidence

ORD record
ord-eeadd77809b647379514a7885aa47ff6
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Reaction notes

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