Water → 2-Methylindole-4-acetic Acid

HRID 11402Notes

Reaction equation

HRID 11402 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:17][C:18]([OH:20])=[O:19])[C:11]=2[CH:10]=[C:9]1[CH3:21])=O)(C)(C)C.O.[OH-].[Na+]>CO>[CH3:21][C:9]1[NH:8][C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:17][C:18]([OH:20])=[O:19])[C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 219744891-t-Butoxycarbonyl-2-methylindole-4-acetic Acid

Product 1

HCID 99205892-Methylindole-4-acetic AcidYield 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-t-butoxycarbonyl-2-methylindole-4-acetic acid (96.3 g) in methanol (200 ml)-water (100 ml) was added dropwise 5N aqueous solution of sodium hydroxide (200 ml) at room temperature, and the mixture was stirred at 50° C. for 3 hours and then stirred at room temperature for 12 hours. The reaction mixture was extracted with hexane-ether. The aqueous layer was adjusted to acidic condition with hydrochloric acid and then extracted with ethyl acetate. The extraction was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure to give the title compound (53.9 g; crude).

Workup

  1. stirringstirred at room temperature for 12 hours
  2. extractionThe reaction mixture was extracted with hexane-ether
  3. extractionextracted with ethyl acetate
  4. extractionThe extraction
  5. washwas washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c174ab2d22d7462da09df0f9e3a20ca3
Source dataset
uspto-grants-2006_08
Patent number
US07098234B2

Reaction notes

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