Hydrochloric Acid → 1-(4-Methoxyphenyl)-1H-indole-2-carboxylic acid

HRID 1071670Notes

Reaction equation

HRID 1071670 reaction equation
C[O:2][C:3]([C:5]1[N:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[C:5]2[C:3]([OH:4])=[O:2])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68858611HCID 68858611, compound

Product 1

HCID 223944961-(4-Methoxyphenyl)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3 g 1-(4-Methoxy-phenyl)-1H-indole-2-carboxylic acid methyl ester in 50 ml THF, 10 ml water and 0.58 g lithium hydroxide monohydrate were added. After stirring for 2 h at 60° C. the reaction was cooled to RT. The mixture was acidified with half concentrated hydrochloric acid and the precipitate was collected by filtration and was washed with 10 ml water The product was obtained as a white solid which was dried under reduced pressure. Yield: 520 mg.

Workup

  1. temperaturewas cooled to RT
  2. filtrationthe precipitate was collected by filtration
  3. washwas washed with 10 ml water The product
  4. customwas obtained as a white solid which
  5. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-199da6eb56644b0981dc2c57ecd36058
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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