Ethanol → HCID 67185016, compound

HRID 868842Notes

Reaction equation

HRID 868842 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4](CC#N)=[CH:3]1.[OH-:15].[K+].[CH2:17]([OH:19])[CH3:18]>O>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:18][C:17]([OH:15])=[O:19])=[CH:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 67187925HCID 67187925, compound

Product 1

HCID 67185016HCID 67185016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(1,4-Dimethyl-1H-indol-3-yl)-acetonitrile (6.0 g, 33 mmol) is suspended in ethanol (150 mL) and then potassium hydroxide (10.6 g, 162 mmol) in water (150 mL) is added to the solution. The reaction is stirred and then heated to reflux for 16 hours. the reaction is then cooled to room temperature and diluted with water. The aqueous layer is washed with DCM (3×150 mL) and then the water layer is cooled to zero and acidified with the addition of 12N HCl. The resulting suspension is extracted with DCM (3×100 mL) and the organic layers are combined, filtered and evaporated in vacuo. The resulting product is used without further purification (3.9 g, 20 mmol, 60%) LC/MS (M++1): 204.7.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. washThe aqueous layer is washed with DCM (3×150 mL)
  4. temperaturethe water layer is cooled to zero
  5. additionacidified with the addition of 12N HCl
  6. extractionThe resulting suspension is extracted with DCM (3×100 mL)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe resulting product is used without further purification (3.9 g, 20 mmol, 60%) LC/MS (M++1)

Sources & evidence

ORD record
ord-1a5f877132aa4a43b096dd22a1be286e
Source dataset
uspto-grants-2015_03
Patent number
US08969348B2

Reaction notes

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