Hydrochloric Acid → 1-(1-Methylethyl)-1H-indole-3-carboxylic acid

HRID 1372692Notes

Reaction equation

HRID 1372692 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15]C)=[O:14])=[CH:5]1)([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10443342Methyl 1-(1-methylethyl)-1H-indole-3-carboxylate

Product 1

HCID 103979731-(1-Methylethyl)-1H-indole-3-carboxylic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In THF (8.0 ml) was dissolved methyl 1-isopropylindole-3-carboxylate (387.6 mg, 1.784 mmol). To the resulting solution was added 0.25N NaOH (8.0 ml). The resulting mixture was stirred at 50° C. for 18 hours. After cooling to room temperature, the reaction mixture was acidified 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-isopropylindole-3-carboxylic acid (327.8 mg, 90%) as a pale pink amorphous substance.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe crystals thus precipitated
  3. filtrationwere collected by filtration under reduced pressure
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-65d9c0157ad14ecfb548ad0e660868ee
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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