Hydrochloric Acid → 1-Butylindoline-6-carboxylic acid

HRID 348951

Reaction equation

HRID 348951 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21086137Methyl 1-butylindoline-6-carboxylate

Product 1

HCID 210851761-Butylindoline-6-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of Methyl 1-butylindoline-6-carboxylate (1.6 g) in methanol (20 mL) was added 1N NaOH (5.0 mL). The mixture was heated at 60° C. for 2 h then cooled to room temperature, poured into 1N HCl and extracted into ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and concentrated to give 1.16 g of the title compound: 1H NMR (CDCl3) δ 0.974, 1.43, 1.60, 3.01, 3.11, 3.42, 7.1, 7.43.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted into ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14412c7ca1144ab284fbc28f05b7c03a
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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