Water → N-acetyl-3-phenylindoline

HRID 262291Notes

Reaction equation

HRID 262291 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-fd9bb74308fb497badfb14f6bc31f721
Source dataset
uspto-grants-1979_05
Patent number
US04153789

Reaction notes

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