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

HRID 1762467Notes

Reaction equation

HRID 1762467 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]1(=O)[O:11][C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12>C1(C)C=CC=CC=1>[OH:5][CH2:4][CH2:3][CH2:2][N:1]1[C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]2[C:6]1=[O:11]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 90863-Amino-1-propanol

Product 1

HCID 701602-(3-Hydroxypropyl)isoindoline-1,3-dioneYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 18.95 g (0.25 mo.) of 3-aminopropanol and 37.0 g (0.25 mol) of phthalic anhydride in 25 ml of dry toluene was refluxed for three hours using a Dean-Stark apparatus. The mixture was cooled, concentrated in vacuo, dissolved in dichloromethane and washed with water. The evaporated organic phase was dried over magnesium sulfate, concentrated in vacuo, and distilled at 183°-184° C. (0.1 mm Hg) to give 28.18 g (55%) of a white solid; m.p. 75°-77° C.; NMR: (CDCl3) δ 1.9 (2H,q), 3.65 (5H,m), 7.6 (4H,s).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe evaporated organic phase was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationdistilled at 183°-184° C. (0.1 mm Hg)

Sources & evidence

ORD record
ord-cec59e56d04e4d5bb50e3896385aecc2
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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