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

HRID 1406727Notes

Reaction equation

HRID 1406727 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-029e6df89e7d4dc8b1adac8411f8d0d9
Source dataset
uspto-grants-2014_12
Patent number
US08916552B2

Reaction notes

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