Water → N-acetyl-3-phenylindoline

HRID 1679274Notes

Reaction equation

HRID 1679274 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Na+].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:19]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1)(=[O:21])[CH3:20]

Participants

5

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 109323533-phenyl-2,3-dihydro-1H-indole

Product 1

HCID 15428722N-acetyl-3-phenylindoline

Procedure

1.0 G of 3-phenylindoline was dissolved in 10 ml of acetic anhydride at room temperature. After 10 minutes, the reaction mixture was poured into 100 ml of water, slightly basified with aqueous sodium hydroxide and extracted with methylene chloride. After removal of the methylenechloride, the residue was recrystallized from cyclohexane to give 1.15 g of the desired N-acetyl-3-phenylindoline which was found to have a 106°-7° C.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter removal of the methylenechloride
  3. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-2d6b61be50b84b52b1ac368ad7d40746
Source dataset
uspto-grants-1978_03
Patent number
US04080330

Reaction notes

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