Sodium Hydroxide → 6-hydroxy-1-ethyl-1H-indole-3-carbonitrile

HRID 907089Notes

Reaction equation

HRID 907089 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[C:5]([C:14]#[N:15])=[CH:4]1)[CH3:2].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH:12][C:9]1[CH:10]=[C:11]2[C:6]([C:5]([C:14]#[N:15])=[CH:4][N:3]2[CH2:1][CH3:2])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 594250606-hydroxy-1-ethyl-1H-indole-3-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (2.85 g, 14.2 mmol), prepared by example 1A, step B, in CH2Cl2 (40 mL) was added a 1M solution of BBr3 in CH2Cl2 (28.5 mL, 28.5 mmol) at 0° C. The mixture was allowed to warm to room temperature and kept for 2.5 h. The dark reaction mixture was then poured onto ice and sufficient 1M NaOH was added until the pH was 8-9. The product was extracted with CH2Cl2 (3×) and the combined organic phases were washed with saturated NaHCO3 , H2O and saturated NaCl. After drying over MgSO4, the solution was concentrated and the product was purified by chromatography (EtOAc/CH2Cl2, 0-10%) to afford 2.15 g (82%) of 6-hydoxy-1-ethyl-1H-indole-3-carbonitrile as a yellow solid.

Workup

  1. customThe dark reaction mixture
  2. additionwas added until the pH was 8-9
  3. extractionThe product was extracted with CH2Cl2 (3×)
  4. washthe combined organic phases were washed with saturated NaHCO3 , H2O and saturated NaCl
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe solution was concentrated
  7. customthe product was purified by chromatography (EtOAc/CH2Cl2, 0-10%)

Sources & evidence

ORD record
ord-ce69b1ff6386496c96a04ecb2efff881
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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