Phthalic Anhydride → 2-(2-(2-Oxoindolin-3-yl)ethyl)isoindoline-1,3-dione

HRID 1749527Notes

Reaction equation

HRID 1749527 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:14].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12>C1(C)C=CC=CC=1.CN1C(=O)CCC1>[O:14]=[C:6]1[CH:5]([CH2:4][CH2:3][N:2]2[C:18](=[O:19])[C:17]3[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15]2=[O:20])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 117012923-(2-aminoethyl)-2,3-dihydro-1H-indol-2-one hydrochloride

Product 1

HCID 1181621082-(2-(2-Oxoindolin-3-yl)ethyl)isoindoline-1,3-dioneYield 56.4%

Reagents, catalysts & solvents 1

HCID 21877177toluene N-methylpyrrolidoneSolvent

Procedure

A mixture of 3-(2-aminoethyl)indolin-2-one hydrochloride (3.20 g, 15.06 mmol), phthalic anhydride (3.34 g, 22.59 mmol) and TEA (4.56 g, 45.18 mmol) in toluene/NMP (20 mL/10 mL). The mixture was heated under reflux for 3 h. The reaction mixture was concentrated and the resulting mixture was washed with saturated aqueous ammonium chloride and brine. The separated organic layer was dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (30% ethyl acetate in petroleum ether) to afford the title compound (2.60 g, 8.50 mmol, 56% yield) as a brown solid. MS (ESI) m/z 307.2 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. washthe resulting mixture was washed with saturated aqueous ammonium chloride and brine
  5. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationConcentration under vacuum
  8. customgave the crude product, which
  9. customwas purified by silica gel column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-461153b79e1e45dba12ce8d99d44aadf
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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