Hydrochloric Acid → 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylic acid

HRID 2249652Notes

Reaction equation

HRID 2249652 reaction equation
[CH2:1]([O:5][C:6]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:28][C:7]=1[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]([C:23]([O:25]CC)=[O:24])=[CH:13]2)=[O:9])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].O.Cl>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:28][C:7]=1[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]([C:23]([OH:25])=[O:24])=[CH:13]2)=[O:9])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 17816510ethyl 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylate

Product 1

HCID 178164505-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylic acidYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

In 2 ml of ethanol is dissolved 0.18 g of ethyl 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylate. After adding 0.3 ml of 5 mol/L sodium hydroxide, the mixture thus obtained is stirred at ambient temperature for one hour. Water and chloroform are added to the reaction mixture, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1). Thus, 0.15 g of 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylic acid is obtained as a white solid product.

Workup

  1. customthe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c3d994a116404c4d804fa22e8e7115f0
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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