Nitric Acid → 1-(2,6-Dichloro-phenyl)-5-nitro-1,3-dihydro-indol-2-one

HRID 1807432Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]1=[O:18].[N+:19]([O-])([OH:21])=[O:20]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[CH:15][CH:16]=2)[CH2:11][C:10]1=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

600 mg 1-(2,6-dichloro-phenyl)-1,3-dihydro-indol-2-one are dissolved in 5 ml concentrated sulphuric acid and cooled to 0° C. To this is added dropwise a solution of 160 μl concentrated nitric acid in 1 ml concentrated sulphuric acid. The mixture is stirred for 30 minutes and then added to 50 g ice. Then the mixture is stirred for 1 hour and the solid is suction filtered. After drying in vacuo the solid is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 20:80).

Workup

stirringThen the mixture is stirred for 1 hour
filtrationfiltered
customAfter drying in vacuo the solid
customis chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 20:80)

Sources & evidence

ORD record: ord-80e3a4aec220416faac1704455923f8e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357689B2

Reaction notes

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