Ethanol → 7-(alpha-Acetylbenzyl) indoline

HRID 267238Notes

Reaction equation

HRID 267238 reaction equation
[CH3:1][C:2]1[N:11]2[C:12]3[C:8]([CH2:9][CH2:10]2)=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([OH:21])C.S(=O)(=O)(O)O.[OH-].[Na+]>O>[C:2]([CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH2:10][CH2:9]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])[CH3:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 112417811,2-Dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole

Product 1

HCID 215559817-(alpha-Acetylbenzyl) indoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.0 g. (0.0258 mole) of 1,2-dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole in 60 ml. of ethanol, 30 ml. of water and 30 ml. of conc. sulfuric acid was refluxed for one hour. The hot solution was poured into a cold concentrated sodium hydroxide solution and the basic solution was extracted several times with ether. The combined ether extracts were washed with water, dried over sodium sulfate and concentrated at reduced pressure. The residual oil solidified and was recrystallized from petroleum ether to give 7-(α-acetylbenzyl) indoline which melted at 55°-56°C.

Workup

  1. additionA mixture of 6.0 g
  2. extractionthe basic solution was extracted several times with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-2439b3ea0eec4f849b9b14921485495e
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

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