Hydrochloric Acid → 6-Methoxy-7-nitroindoline-2,3-dione

HRID 1398956Notes

Reaction equation

Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([C:6](=[O:15])[C:7](=[O:14])[NH:8]2)=[CH:4][CH:3]=1.[CH3:16][O-:17].[Na+].Cl>CO>[CH3:16][O:17][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([C:6](=[O:15])[C:7](=[O:14])[NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-chloro-7-nitro-1H-indole-2,3-dione (2.0 g, 8.83 mmol) in methanol (20 mL) was added a solution of sodium methoxide in methanol (28%, 3.8 mL) at room temperature. The mixture was stirred at 60° C. for 14 hr. 1N Hydrogen chloride (10 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with ethyl acetate. The organic layer was washed with brine (×3), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-100% ethyl acetate/n-hexane gradient mixture to give the title compound (1.349 g, 6.07 mmol, 69%) as a yellow solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine (×3)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with a 30-100% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record: ord-0069d2056a2547ac884c7891e9b7326d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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