Water → 5-Chloro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 492215Notes

Reaction equation

HRID 492215 reaction equation
O.[OH-].[Li+].O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=1)[CH:10]=[C:9]2[C:25]([O:27]C)=[O:26]>O1CCCC1>[C:25]([C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([Cl:5])[CH:7]=2)[N:11]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:10]=1)([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68968651Methyl 5-chloro-1-(quinolin-4-yl)-1H-indole-3-carboxylate

Product 1

HCID 689703725-Chloro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.42 g (15 mmol) of lithium hydroxide monohydrate and 50 cm3 of water are added to 1.13 g (3.35 mmol) of 5-chloro-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-indole dissolved in 50 cm3 of tetrahydrofuran at a temperature in the region of 20° C. After stirring for 16 hours at the reflux temperature of the solvent, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 10 cm3 of 1N hydrochloric acid, the suspension is then filtered, and the solid residue is dried under atmospheric pressure at a temperature in the region of 60° C., giving 0.95 g of 3-carboxy-5-chloro-1-(quinolin-4-yl)-1H-indole in the form of a cream-colored solid, which is used directly in the following step.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. filtrationthe suspension is then filtered
  3. customthe solid residue is dried under atmospheric pressure at a temperature in the region of 60° C.

Sources & evidence

ORD record
ord-4638948873f94f96bf8ceaedb4a9812c
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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