Nitric Acid → 2,2,2-Trichloro-1-(1-methyl-4-nitro-1H-pyrrol-2-yl)ethan-1-one

HRID 1831029Notes

Reaction equation

C(OC(=O)C)(=O)C.[CH3:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:19])[C:15]([Cl:18])([Cl:17])[Cl:16].[N+:20]([O-])([OH:22])=[O:21]>C(O)(C)C>[CH3:8][N:9]1[CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[CH:11]=[C:10]1[C:14](=[O:19])[C:15]([Cl:16])([Cl:17])[Cl:18]

Participants

Conditions

Temperature: -40 °C

Procedure

An acetic anhydride solution (200 ml) containing 3 (45.2 g, 0.200 mol) was cooled to −40° C., and then fuming nitric acid (18.5 ml, 0.360 mol) was dropped into the solution at the same temperature. After stirring the mixture for 2 hours at a room temperature, isopropanol was added to precipitate a solid. The precipitated solid was collected by filtration to obtain a nitro substance 5 (27.2 g). The filtrate was distilled under a reduced pressure, and the obtained residue was subjected to silica gel column chromatography to further obtain 5 (10.7 g) from an elusion position of ethyl acetate-hexane (1:10, v/v). (Total yield: 70%)

Workup

customto precipitate a solid
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-e3fc111ae3f845cfaf886ae48fab0e9e
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067622B2

Reaction notes

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