Dimethylformamide → 2-[3-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propyl]isoindole-1,3-dione

HRID 1978005Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][CH2:7][CH:6]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K].CN(C=O)C>O>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9]([CH2:8][CH2:7][CH:6]=[C:5]2[CH2:4][CH2:3][CH2:2][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(3-bromopropyl)-6-methoxy-1,2-dihydronaphthalene (10 g, 35.6 mmol), potassium phthalimide (7.9 g, 42.7 mmol) and DMF (50 ml ) was heated at 100° C. for 1 hour and then cooled. The mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with brine and water, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:8) to afford the titled compound (11.8 g, yield 95%, oil).

Workup

temperaturecooled
extractionthe product was extracted with ethyl acetate
washThe extract was washed with brine and water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed in vacuo
customThe residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record: ord-310b8a358cd847009b8e2b8c416d0584
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235789B1

Reaction notes

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