Hydrochloric Acid → 1-(4-Fluorophenyl)-1h-indole-5-carboxylic acid

HRID 401618Notes

Reaction equation

HRID 401618 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.O[Li].O.Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59625729Methyl 1-(4-fluorophenyl)-1h-indole-5-carboxylate

Product 1

HCID 226030711-(4-Fluorophenyl)-1h-indole-5-carboxylic acidYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 1-(4-fluorophenyl)-indole-5-carboxylate 1m (0.58 g, 2.15 mmol) and LiOH H2O (0.36 g, 8.6 mmol) in THF (15 mL) and H2O (10 mL) was stirred at room temperature for 5 days. Aqueous 10% HCl solution was added to the reaction mixture to adjust pH=3˜4. The resulting mixture was extracted with EtOAc (2×). The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated to give 1n (0.5 g).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×)
  2. washThe organic solution was washed with aq. NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f00b5dd7e7ed4704ae2eb3ecd0f08fa3
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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