HCID 22285066, compound → 7-bromo-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one

HRID 1061885Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[CH:7](O)[N:8]([CH3:14])[C:9](=[O:13])[C:10]=3[CH:11]=[CH:12][C:4]=2[CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[CH2:7][N:8]([CH3:14])[C:9](=[O:13])[C:10]=3[CH:11]=[CH:12][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-Bromo-1-hydroxy-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one (1.03 g) was dissolved in acetic acid (25 ml) and zinc (3.0 g) was added. The mixture was stirred with heating at 100° C. for 3 hrs. The reaction mixture was filtered through celite and the filtrate was concentrated. The obtained residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extracted layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (carrier: silica gel, developing solvent: hexane-ethyl acetate, 2:1-1:1). The obtained crystals were washed with diisopropyl ether to give the title compound (0.84 g) as colorless crystals.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated
additionThe obtained residue was diluted with saturated aqueous sodium hydrogen carbonate
extractionextracted with ethyl acetate
dry with materialThe extracted layer was dried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography (carrier: silica gel, developing solvent: hexane-ethyl acetate, 2:1-1:1)
washThe obtained crystals were washed with diisopropyl ether

Sources & evidence

ORD record: ord-c920cc83dc5e4f8b94829ac43959e0db
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960586B2

Reaction notes

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