Nitric Acid → N-[4-fluoro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

HRID 53788Notes

Reaction equation

HRID 53788 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12]([F:15])([F:13])[F:14])[C:8]([F:11])=[CH:9][C:10]=1[N+:16]([O-:18])=[O:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10353438Acetamide, N-[4-fluoro-3-(trifluoromethyl)phenyl]-

Product 1

HCID 10015744N-[4-fluoro-2-nitro-5-(trifluoromethyl)phenyl]acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 3-acetamido-6-fluorobenzotrifluoride (2.4 g, 10.85 mmol) in concentrated H2SO4 (10 mL) at 0° C. was added dropwise 70% HNO3 (1.5 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 (20 g). The precipitate was collected by filtration, affording 2.6 g (90%) of crude 3-acetamido-6-fluoro-4-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to give 2.1 g of pure compound as yellow needles. 1H NMR (CDCl3): δ 2.318 (s, 3H), 8.062 (d, 1H, J=9.6 Hz), 9.196 (s, 1H), 10.152 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-0c9659438d2f4a1e992e9a6f21225d99
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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