Methanol → 2-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetic acid

HRID 850642Notes

Reaction equation

HRID 850642 reaction equation
[OH-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([Br:26])[CH:24]=4)[N:19]([CH3:27])[CH:18]=3)[C:13]([O:15]C)=[O:14])=[CH:11][C:6]=2[O:5][CH2:4]1.CO>O1CCOCC1>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([Br:26])[CH:24]=4)[N:19]([CH3:27])[CH:18]=3)[C:13]([OH:15])=[O:14])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22467212Methyl 2-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetate

Product 1

HCID 224672612-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous sodium hydroxide (14.7 ml of 1M) was added to a solution of methyl 2-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetate from (b) (1.97 g, 4.9 mmol) in a 3:1 mixture of methanol and 1,4-dioxane at ambient temperature. The mixture was heated to reflux for 1 hour before recooling and removing the organic solvents in vacuo. The residue was redissolved in water and acidified with drops of concentrated hydrochloric acid. The resultant precipitate was extracted with diethylether, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was crystallised from diisopropylether to give the subtitle compound (1.59 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour before recooling
  3. customremoving the organic solvents in vacuo
  4. dissolutionThe residue was redissolved in water
  5. extractionThe resultant precipitate was extracted with diethylether
  6. dry with materialdried (magnesium sulphate)
  7. customthe solvent removed in vacuo
  8. customThe residue was crystallised from diisopropylether

Sources & evidence

ORD record
ord-b5da0d6964e34637b1442dccd68a18dd
Source dataset
uspto-grants-2000_01
Patent number
US06017945

Reaction notes

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