Nitric Acid → N-[4-chloro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

HRID 439482Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[C:12]([F:15])([F:14])[F:13])(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[C:10]([N+:16]([O-:18])=[O:17])=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[C:12]([F:15])([F:13])[F:14])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-acetamido-5-chlorobenzotrifluoride (890 mg, 3.74 mmol) in concentrated H2SO4 (4 mL) at 0° C. was added dropwise 70% HNO3 (0.5 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (15 g). The precipitate was collected by filtration, affording 700 mg of crude 2-acetamido-5-chloro-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to give 559 mg of pure 2-acetamido-5-chloro-3-nitrobenzotrifluoride as yellow needles. Mp 190°-2° C., 1H NMR (CDCl3): δ2.210 (s, 3H), 7.357 (s, 1H), 7.896 (d, 1H, J=2.1 Hz), 8.105 (d, 1H, J=2.1 Hz).

Workup

waitat room temperature for 3 h
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-4a36cdb855994188b140b88b03441a5f
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514680

Reaction notes

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