Phthalic Anhydride → 2-(4,5-Dimethyl-2-pyridinyl)-1H-isoindole-1,3(2H)-dione

HRID 869890Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.[C:10]1(=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[O:11]1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([N:9]2[C:10](=[O:11])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:19])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4,5-dimethylpyridin-2-amine (2.1 g, 0.02 mol) in acetic acid (40 mL) was added isobenzofuran-1,3-dione (2.5 g, 0.02 mol) at the room temperature. The mixture was heated at 90° C. overnight. The resulting solution was basified by saturated solution of NaHCO3 and extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give 2-(4,5-dimethylpyridin-2-yl)-isoindoline-1,3-dione (1.7 g, 40%) 1H NMR (300 MHz, DMSO) δ 8.33 (s, 1H), 7.97-7.91 (m, 4H), 7.32 (s, 1H), 2.30 (s, 3H), 2.27 (s, 3H).

Workup

extractionextracted with ethyl acetate (50 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
customevaporated under vacuum

Sources & evidence

ORD record: ord-64f855316c25441c9979e7b59c08ffd1
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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