Hydrochloric Acid → 3-butyl-1H-indole-5-carboxylic acid

HRID 14215

Reaction equation

HRID 14215 reaction equation
[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]CC)=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21086100ethyl 3-butyl-1H-indole-5-carboxylate

Product 1

HCID 210857253-butyl-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of Ethyl 3-butyl-1H-indole-5-carboxylate, Example SP-225, step 2, (0.4 g) in methanol (15 mL) was added 1N NaOH (5 mL). The mixture was stirred at 50° C. for 18 h, cooled to room temperature and poured into 1N HCl (50 mL). The mixture was extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give 0.145 g of the title compound: MS (ESI+) for C13H15N1O2 m/z 216.12 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4263dc9fd126413093338397035c2054
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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