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

HRID 505988Notes

Reaction equation

HRID 505988 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) is added a 1M solution of BBr3 in CH2Cl2 (28.5 mL, 28.5 mmol) at 0° C. The mixture is allowed to warm to room temperature and kept for 2.5 h. The dark reaction mixture is then poured onto ice and sufficient 1M NaOH is added until the pH is 8-9. The product is extracted with CH2Cl2 (3×) and the combined organic phases are washed with saturated NaHCO3, H2O and saturated NaCl. After drying over MgSO4, the solution is concentrated and the product is 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. additionis added until the pH is 8-9
  3. extractionThe product is extracted with CH2Cl2 (3×)
  4. washthe combined organic phases are washed with saturated NaHCO3, H2O and saturated NaCl
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe solution is concentrated
  7. customthe product is purified by chromatography (EtOAc/CH2Cl2, 0-10%)

Sources & evidence

ORD record
ord-5dd882515b974021a35f5c194cf5eb5a
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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