Phthalic Anhydride → 2-(2-(2-Oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione

HRID 1410039Notes

Reaction equation

Br.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[CH:6]=1.[C:12]1(=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[O:13]1.CCN(C(C)C)C(C)C>C1(C)C(C)=CC=CC=1>[O:11]=[C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][N:2]2[C:12](=[O:13])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:21])[CH:10]=[CH:9][NH:8]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-(2-aminoethyl)pyridin-2(1H)-one hydrobromide (400 mg, 1.83 mmol), isobenzofuran-1,3-dione (271 mg, 1.83 mmol) and DIEA (472 mg, 3.66 mmol) in 30 mL of xylene was stirred at 140° C. for 6 hours. The solvent was removed under reduce pressure. The residue was purified by silica gel chromatography, eluting with DCM/MeOH (30/1) to give 2-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione (370 mg, 76%) as a white sold. LC-MS: 269 [M+H]+, tR=1.23 min.

Workup

customThe solvent was removed
customThe residue was purified by silica gel chromatography
washeluting with DCM/MeOH (30/1)

Sources & evidence

ORD record: ord-d8e7b8022f5342a5b911bd180d829a1c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Reaction notes

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