Hydrochloric Acid → 1-ethyl-1H-indole-3-carboxylic acid

HRID 1372688Notes

Reaction equation

HRID 1372688 reaction equation
[OH-].[Na+].Cl.[CH2:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17]C)=[O:16])=[CH:7]1)[CH3:5]>C1COCC1>[CH2:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([OH:17])=[O:16])=[CH:7]1)[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 5191495Methyl 1-ethylindole-3-carboxylate

Product 1

HCID 36971601-ethyl-1H-indole-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In THF (9.0 ml) was dissolved the methyl 1-ethylindole-3-carboxylate obtained in the above-described (Step 1). To the resulting solution was added 0.25N NaOH (9.0 ml) at room temperature. After the reaction mixture was stirred at 50° C. for 36 hours, 1N NaOH (1.0 ml) was added thereto, followed by stirring at 70° C. for 9 hours. The reaction mixture was cooled to room temperature, and then neutralized with 1N HCl (4.5 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 1-ethylindole-3-carboxylic acid (388.0 mg, 90%, yield of 2 steps) as a pale pink amorphous substance.

Workup

  1. customobtained in the above-described (Step 1)
  2. stirringby stirring at 70° C. for 9 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-af1ffb82734b4e67a4e8e17d95ece895
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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