Hydrochloric Acid → 3-Butyl-1-methyl-1H-indole-5-carboxylic acid

HRID 14213Notes

Reaction equation

HRID 14213 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)[N:7]([CH3:19])[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)[N:7]([CH3:19])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21086101Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate

Product 1

HCID 210857263-Butyl-1-methyl-1H-indole-5-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate (0.294 g) in methanol (20 mL) was added 1N NaOH (10 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 and the ethyl acetate extract was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give 0.234 g (89%) of the title compound: 1H NMR (CD3OD) δ 0.965, 1.42, 1.69, 2.76, 3.77, 7.02, 7.35, 7.84, 8.29.

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-9d2835a08c0c4cf0bf017d1160dab88b
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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