Hydrochloric Acid → HCID 261193, compound

HRID 1417462Notes

Reaction equation

HRID 1417462 reaction equation
[OH-].[K+].[CH3:3][C:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][C:5]=1[C:17]([O:19]CC)=[O:18].Cl>C(O)C>[CH3:3][C:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][C:5]=1[C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2549779H-Carbazole-2-carboxylic acid, 1-methyl-, ethyl ester

Product 1

HCID 261193HCID 261193, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 ml of ethanol and 4 ml of a 2N aqueous solution of potassium hydroxide were added to 100 mg of ethyl 1-methylcarbazole-2-carboxylate (obtained according to the procedures described in C. J. Moody and K. F. Rahimtoola, J. Chem. Soc. Parkin. Trans. I, 673 (1990)]. The reaction mixture was stirred for 2 hours at room temperature, and then acidified by the addition of a 1N aqueous solution of hydrochloric acid, after which it was concentrated by evaporation under reduced pressure. Ethyl acetate was added to the residue. The aqueous layer was extracted with ethyl acetate, and the organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was recrystallized from ethyl acetate and hexane, to yield 81 mg of the title compound, melting at >240° C.

Workup

  1. customobtained
  2. concentrationafter which it was concentrated by evaporation under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. extractionthe organic extract
  6. washwas washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe resulting residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-e9ad59347caa4a6cbc6a941eb77a3c45
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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