Phthalic Anhydride → 2-(3-Hydroxypropyl)isoindoline-1,3-dione

HRID 522923Notes

Reaction equation

HRID 522923 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]1(=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[O:7]1.CCN(CC)CC>C1(C)C=CC=CC=1>[OH:5][CH2:4][CH2:3][CH2:2][N:1]1[C:6](=[O:7])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:15]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 90863-Amino-1-propanol

Product 1

HCID 701602-(3-Hydroxypropyl)isoindoline-1,3-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-aminopropan-1-ol (1.0 g, 13.1 mmol) and isobenzofuran-1,3-dione (2.0 g, 13.1 mmol) in toluene (25 mL, 3 mL/mmol) was added Et3N (2 mL, 13.1 mmol) and the reaction was heated at reflux for 24 h. Then reaction was quenched with water and extracted with EtOAc (2×40 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 2-(3-hydroxypropyl)isoindoline-1,3-dione (1.8 g, 87%). Observed mass (M+1): 206.1. This material was taken to the next step without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 h
  3. customThen reaction
  4. customwas quenched with water
  5. extractionextracted with EtOAc (2×40 mL)
  6. washThe organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b1b733fe31b42c7aa5f71021a5082f9
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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