Sulfuric Acid → 5,7-Di-tert-butyl-1H-indole-2,3-dione

HRID 1784965Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[NH:15][C:16](=[O:20])/[CH:17]=N/O)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:22]>>[C:11]([C:9]1[CH:8]=[C:7]2[C:6](=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)[NH:15][C:16](=[O:20])[C:17]2=[O:22])([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 87441566HCID 87441566, compound

Product 1

HCID 684075765,7-Di-tert-butyl-1H-indole-2,3-dioneYield 42%

Conditions

Temperature: 0 °C

Procedure

N-(2,4-Di-tert-butyl-phenyl)-2-[(E)-hydroxyimino]-acetamide (500 mg, 1.7 mmol) in concentrated sulfuric acid (3.8 mL) was heated at 90° C. for 2 h. This solution was cooled at 0° C. and slowly added to ice-water (15 mL), the brown precipitate was filtered off and purified by chromatography on silica gel with a gradient of 0% to 25% of ethyl acetate in heptane to afford 200 mg (42%) of an orange powder, MS: m/z=259 (M).

Workup

filtrationthe brown precipitate was filtered off
custompurified by chromatography on silica gel with a gradient of 0% to 25% of ethyl acetate in heptane

Sources & evidence

ORD record: ord-0f8784a802314aa1a0ca0cfde41711cd
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504428B2

Reaction notes

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