Phthalic Anhydride → 1H-Isoindole-1,3(2H)-dione, 2-(2,5-dimethoxyphenyl)-

HRID 1373758Notes

Reaction equation

HRID 1373758 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>CC(C)=O>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[N:5]1[C:15](=[O:16])[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]1=[O:17]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 76132,5-Dimethoxyaniline

Product 1

HCID 9105031H-Isoindole-1,3(2H)-dione, 2-(2,5-dimethoxyphenyl)-Yield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
185 °C

Procedure

2,5-dimethoxyaniline (9.96 g, 65.00 mmol) and phthalic anhydride (10.11 g, 68.25 mmol) were mixed, and heated at 185° C. for 15 minutes under N2. After the reaction mixture was cooled, acetone (50 mL) was added. The precipitate was ultrasonicated, filtered, washed with ethyl acetate (10 mL×2), and dried to give the title compound (17.5 g, 95%). MS (ESI) m/z 283.91 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 3.75 (s, 3 H) 3.79 (s, 3 H) 6.83 (t, J=1.70 Hz, 1 H) 6.98 (d, J=1.70 Hz, 2 H) 7.74–7.81 (m, 2 H) 7.91–7.98 (m, 2 H).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. customThe precipitate was ultrasonicated
  3. filtrationfiltered
  4. washwashed with ethyl acetate (10 mL×2)
  5. customdried

Sources & evidence

ORD record
ord-4e580abcbdcb42548541c9ff1096beab
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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