Sodium Hydroxide → 2,3-Dimethyl-1H-indol-5-ol

HRID 454090Notes

Reaction equation

HRID 454090 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([O:12]C)=[CH:6][CH:5]=2.B(Br)(Br)Br.[OH-].[Na+]>O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([OH:12])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 1647381H-Indole, 5-methoxy-2,3-dimethyl-

Product 1

HCID 220307882,3-Dimethyl-1H-indol-5-olYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2,3-dimethyl-5-methoxyindole (175 mg, 1 mmol), (J. Chem. Soc. 1957, 3175-3180) in methylene (5 ml) cooled at −60° C. was added boron tribromide (210 μl, 2.2 mmol) dropwise. After completion of addition, the mixture was left to warm up to ambient temperature and was stirred for 1 hour. Water was added and the pH was adjusted to 6 with 2N sodium hydroxide. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried (MgSO4) and evaporated to give 2,3-dimethyl-5-hydroxyindole (124 mg, 77%).

Workup

  1. additionAfter completion of addition
  2. waitthe mixture was left
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-52c40622d13648c794e1642c2cd6b915
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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