Sodium Hydroxide → 3-phenyl-2,3-dihydro-1H-indole

HRID 1585218Notes

Reaction equation

HRID 1585218 reaction equation
C([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>O.C(O)C>[C:18]1([CH:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9][CH2:10]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15428721HCID 15428721, compound

Product 1

HCID 109323533-phenyl-2,3-dihydro-1H-indoleYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The amount, 5.50 g, of the 1-benzoyl-3-phenylindoline obtained in Example 6 and a solution of 4.0 g of sodium hydroxide in 40 ml of water and 84 ml of ethanol added thereto were refluxed together for six hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous potassium carbonate solution, then dried over anhydrous magnesium sulfate, and distilled to expel the ethyl acetate and obtain 3.49 g of 3-phenylindoline (97.2%) in the form of an oily semi-solid substance.

Workup

  1. temperaturethereto were refluxed together for six hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous potassium carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled

Sources & evidence

ORD record
ord-b166b44c267949b0a42921815121eaa2
Source dataset
uspto-grants-1999_08
Patent number
US05936098

Reaction notes

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