Phthalimidoacetone → 2-[(3E)-4-(dimethylamino)-2-oxobut-3-en-1-yl]-2,3-dihydro-1H-isoindole-1,3-dione

HRID 64292Notes

Reaction equation

[O:1]=[C:2]([CH3:15])[CH2:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14]>CN(C(OC)OC)C>[CH3:3][N:4]([CH3:12])/[CH:5]=[CH:15]/[C:2](=[O:1])[CH2:3][N:4]1[C:5](=[O:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]1=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(2-oxopropyl)isoindoline-1,3-dione (1 g, 4.9 mmol) in 20 mL of DMF-DMA was added some of 4 A molecular sieve. The reaction mixture was stirred at 100° C. under N2 for 15 hr. After cooling down to RT, the mixture was filtered and collected 600 mg (47.5%) of crude (E)-2-(4-(dimethylamino)-2-oxobut-3-enyl) isoindoline-1,3-dione as a solid. MS (ESI) m/e [M+1]+ 259.1.

Workup

temperatureAfter cooling down to RT
filtrationthe mixture was filtered
customcollected 600 mg (47.5%) of crude (E)-2-(4-(dimethylamino)-2-oxobut-3-enyl) isoindoline-1,3-dione as a solid

Sources & evidence

ORD record: ord-87f8844152cf46b398ed7f18217b40d3
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447106B2

Reaction notes

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