Acetic Acid → 4-Hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione

HRID 334907

Reaction equation

HRID 334907 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C(O)(=O)C>O>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:3]=1[C:8](=[O:9])[N:20]([CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)[C:5]2=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 965803-Hydroxyphthalic anhydride

Product 1

HCID 592631454-Hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dioneYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-hydroxyphthalic anhydride (543 mg, 3.31 mmol), 4-methoxybenzylamine (0.43 mL, 3.31 mmol) and acetic acid (3 mL) was heated at 100° C. for 4 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (760 mg, 81%). 1H NMR (DMSO-d6) 11.03 (1H, s), 7.61 (1H, dd), 7.28 (1H, d), 7.23-7.19 (3H, m), 6.89-6.86 (2H, m), 4.63 (2H, s), 3.71 (3H, s). MS: [M−H+] 282.

Workup

  1. temperatureto cool
  2. filtrationThe white solid was collected by filtration
  3. washwashed well with water
  4. customdried

Sources & evidence

ORD record
ord-5953d9bd1da144b69a53be63945639e8
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Linked notes

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