Hydrochloric Acid → HCID 18505279, compound

HRID 1357266Notes

Reaction equation

HRID 1357266 reaction equation
[CH2:1]([C:5]1[N:6]([CH3:20])[C:7]2[C:12]([C:13]=1[C:14](=[O:19])C(Cl)(Cl)Cl)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[OH-:21].[Na+].Cl>C1COCC1>[CH2:1]([C:5]1[N:6]([CH3:20])[C:7]2[C:12]([C:13]=1[C:14]([OH:19])=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18505303HCID 18505303, compound

Product 1

HCID 18505279HCID 18505279, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-butyl-1-methyl-1H-indol-3-yl)-2,2,2-trichloro-ethanone (4.87 g, 14.7 mmol), prepared in the previous step, and 1 N NaOH (73.5 mL, 73.5 mmol) in 350 mL of THF was refluxed under nitrogen for 2.25 h. After cooling to room temperature 1 N HCl (80 mL, 80 mmol) was added and then the solvent was removed under reduced pressure. The residue was partitioned between 1 N HCl and methylene chloride. The organic layer was separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-1-methyl-1H-indole-3-carboxylic acid (3.44 g, 100%) as a brown solid, mp 163-165° C.

Workup

  1. temperaturewas refluxed under nitrogen for 2.25 h
  2. additionwas added
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between 1 N HCl and methylene chloride
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted three times with methylene chloride
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bec86ee144cc46678a78ff0ca18a9d2a
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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