1-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)propan-1-one → HCID 20094393, compound

HRID 273841Notes

Reaction equation

HRID 273841 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1CNC(=O)C1.[Br:23][Br-]Br>O1CCCC1.S(=O)(=O)(O)O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:16])[CH:14]([Br:23])[CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 230039711-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)propan-1-one

Product 1

HCID 20094393HCID 20094393, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-acetyl-5-propionylindoline (1.65 g) in tetrahydrofuran (150 ml) were added concentrated sulfuric acid (5 drops) and pyrrolidone hydrotribromide (4.14 g), and the mixture was stirred at room temperature for 16 hours. The insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to give 1.78 g of 1-acetyl-5-(2-bromopropionyl)indoline melting at 140°-142° C.

Workup

  1. filtrationThe insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f18b0b7521a6488896d1ec2f879e7208
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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