Acetic Acid → 2-(2,4-Dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dione

HRID 425168Notes

Reaction equation

HRID 425168 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]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].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:18]([CH2:17][C:16]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=1[O:14][CH3:13])[C:5]2=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 965803-Hydroxyphthalic anhydrideHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 592631282-(2,4-Dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-hydroxyphthalic anhydride (1.24 g, 7.6 mmol), 2,4-dimethoxybenzylamine (1.14 mL, 7.6 mmol) and acetic acid (5 mL) was heated at 80° C. for 24 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 (1.73 g, 73%). 1H NMR (DMSO-d6) 11.00 (1H, s), 7.62 (1H, dd), 7.29 (1H, d), 7.21 (1H, d), 6.90 (1H, d), 6.56 (1H, d), 6.43 (1H, dd), 4.59 (2H, s), 3.79 (3H, s), 3.72 (3H, s). MS: [M−H+]314.

Workup

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

Sources & evidence

ORD record
ord-7cd37a89d5cf4ab798599d54c4b5701e
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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