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

HRID 582197Notes

Reaction equation

HRID 582197 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].O>CN(C)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

5

Reactant 3

HCID 962WaterHCID 104238234-(3-Bromopropyl)-6-methoxy-1,2-dihydronaphthaleneHCID 24194345Phthalimide potassium salt

Product 1

HCID 219964552-[3-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propyl]isoindole-1,3-dioneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-bromopropyl)-1,2-dihydro-6-methoxynaphthalene (10 g, 35.6 mmol.) and potassium phthalimide (7.9 g, 42.7 mmol.) was stirred in N,N-dimethylformamide (50 ml) for one hour at 100° C. The reaction mixture was cooled to room temperature, to which was poured water, then the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue thus obtained was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8) to afford the titled compound (11.8 g, yield 95%, oily).

Workup

  1. extractionthe organic substance was extracted with ethyl acetate
  2. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-7ad19f2a7e7f44ba8e4f06bd43979731
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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