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

HRID 874914Notes

Reaction equation

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

Participants

Conditions

Temperature: -40 °C

Procedure

Nitric acid (90%, 2 mL) was added dropwise over a period of 30 minutes to a solution of 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone (II) (1 g, 4.7 mmol) in acetic anhydride (10 ml), cooled to −40° C. The reaction mixture was allowed to warm up slowly to room temperature and stirred for 6 h. The solvent was evaporated under vacuum and the residue purified by flash chromatography (hexane-EtOAc 9:1) to obtain the compound of formula (III) as a yellow solid (670 mg, 55% yield). 2,2,2-Trichloro-1-(5-nitro-1H-pyrrol-2-yl)ethanone was also obtained as side product (349 mg, 29% yield).

Workup

temperatureto warm up slowly to room temperature
customThe solvent was evaporated under vacuum
customthe residue purified by flash chromatography (hexane-EtOAc 9:1)

Sources & evidence

ORD record: ord-ea885cecc90f487aba3c4a612e0fbdb4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981092B2

Reaction notes

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