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

HRID 1372696Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19]C)=[O:18])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([OH:19])=[O:18])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In THF (15 ml) was dissolved methyl 1-benzylindole-3-carboxylate (606.1 mg, 2.284 mmol). To the resulting solution was added 0.25N NaOH (8.0 ml) and the mixture was stirred at 70° C. for 18 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue thus obtained was acidified with 1N HCl (5.5 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 1-benzylindole-3-carboxylic acid (100%) as a light pink amorphous substance.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
distillationthe solvent was distilled off under reduced pressure
customThe residue thus obtained
customThe crystals thus precipitated
filtrationwere collected by filtration under reduced pressure
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-4466b0197bad4c49ac49474540bb1f7b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

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