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Acetic Acid → 2-(4-(2-Hydroxyethyl)phenyl)isoindoline-1,3-dione

HRID 1023833
Notes
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Reaction equation

HRID 1023833 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.C(O)(=O)C>O>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([N:1]2[C:14](=[O:15])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]2=[O:16])=[CH:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6811Phthalic AnhydrideHCID 669044-Aminophenethyl alcohol

Product 1

HCID 534662882-(4-(2-Hydroxyethyl)phenyl)isoindoline-1,3-dioneYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A flask containing 4-aminophenethyl alcohol (1 g, 7.29 mmol), phthalic anhydride (1.13 g, 7.65 mmol) and acetic acid (6 mL) was heated at 100° C. for 1 h. The reaction mixture was poured into water (50 mL) and the solid was filtered off and washed with water. The crude was purified by flash column chromatography to afford the desired product as white solid (1.2 g, 62%). 1H NMR: 2.92 (t, 2H, J=6.6 Hz), 3.89 (t, 2H, J=6.6 Hz), 7.38 (s, 3H), 7.77-7.82 (m, 2H), 7.92-7.97 (m, 21-1).

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with water
  3. customThe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-a92b966dde684657aa4e3d8e14a16873
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722720B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes