Hydrochloric Acid → 6-Methoxy-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 492204Notes

Reaction equation

HRID 492204 reaction equation
O.[OH-].[Li+].O.[CH3:5][O:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([C:26]([O:28]C)=[O:27])=[CH:12][N:13]2[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)=[CH:9][CH:8]=1.Cl>O1CCCC1>[C:26]([C:11]1[C:10]2[C:14](=[CH:15][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)[N:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH:12]=1)([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68970361Methyl 6-methoxy-1-(quinolin-4-yl)-1H-indole-3-carboxylate

Product 1

HCID 689717576-Methoxy-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.947 g (22.57 mmol) of lithium hydroxide monohydrate and 115 cm3 of water are added at a temperature in the region of 25° C. to 2.5 g (7.52 mmol) of 6-methoxy-3-methoxycarbonyl-1-(quinol-4-yl)-1H-indole dissolved in 115 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 19 hours, the reaction mixture is concentrated under reduced pressure (2.7 kPa) to give a residue which is taken up with 22.5 cm3 of N hydrochloric acid. After filtering off and drying the solid residue at atmospheric pressure at a temperature in the region of 60° C., 2.4 g of 3-carboxy-6-methoxy-1-(quinol-4-yl)-1H-indole are obtained in the form of a beige-coloured solid which decomposes at approximately 175° C.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. filtrationAfter filtering off
  4. dry with materialdrying the solid residue at atmospheric pressure at a temperature in the region of 60° C., 2.4 g of 3-carboxy-6-methoxy-1-(quinol-4-yl)-1H-indole
  5. customare obtained in the form of a beige-coloured solid which
  6. customdecomposes at approximately 175° C.

Sources & evidence

ORD record
ord-3259a873127447d6996c05221a0ddbc1
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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