Hydrochloric Acid → 2-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione

HRID 1071528Notes

Reaction equation

C[C:2]1[CH:13]=[CH:12][C:5]([CH2:6]OS(C)(=O)=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH3:17]N(C=O)C.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K].Cl>CCCCCC.C(OCC)(=O)C>[CH3:17][CH:6]([N:26]1[C:22](=[O:32])[C:23]2[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:25]1=[O:27])[C:5]1[CH:12]=[CH:13][CH:2]=[C:3]([N+:14]([O-:16])=[O:15])[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methanesulfonic acid 4-methyl-3-nitro-benzyl ester (0.45 g, 1.83 mmol) was added to anhydrous DMF (20 mL), under argon, and potassium phthalimide (0.34 g, 1.83 mmol) was added. The reaction mixture was heated to 60° C. for 12 h. The reaction mixture was cooled and poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (4:1 hexane/ethyl acetate) Yield 0.45 g. 1H NMR (CDCl3, 300 MHz): δ 2.58 (s, 3H), 4.88 (s, 2H), 7.30 (d, J=7 Hz, 1H), 7.57 (d, J=7 Hz, 1H), 7.24-7.77 (m, 2H), 7.84-7.89 (m, 2H), 8.02 (s, 1H).

Workup

temperatureThe reaction mixture was cooled
extractionthe aqueous layer was extracted three times with ethyl acetate
washThe combined organic layers were washed with water, brine
dry with materialdried over anhydrous magnesium sulfate
filtrationThe solution was filtered
customthe solvent removed under reduced pressure
customThe product was isolated by flash chromatography

Sources & evidence

ORD record: ord-d20e26f96fa74045a2cd41d8a52b0b07
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906067B2

Reaction notes

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