Sodium Bicarbonate → 5-Fluoro-2-nitro-4-(trifluoromethyl)aniline

HRID 538202Notes

Reaction equation

HRID 538202 reaction equation
[F:1][C:2]1[C:3]([C:15]([F:18])([F:17])[F:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8]C(=O)C)[CH:7]=1.C([O-])(O)=O.[Na+]>Cl>[F:1][C:2]1[C:3]([C:15]([F:16])([F:17])[F:18])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH2:8])[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 10754199N-(5-Fluoro-2-nitro-4-trifluoromethyl-phenyl)-acetamide

Product 1

HCID 106806255-Fluoro-2-nitro-4-(trifluoromethyl)anilineYield 91.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of N-(5-fluoro-2-nitro-4-trifluoromethyl-phenyl)-acetamide (17.8 g, 67.0 mmol) in aqueous HCl (3M, 400 mL) was heated at reflux for 3 h. The resulting suspension was cooled to 0° C. and brought to pH 8 with NaHCO3. The resulting solid was collected to yield the titled compound (13.7 g, 91% yield). The compound did not yield MS data. 1H NMR (400 MHz, CDCl3): 8.48 (d, J=7.3 Hz, 1H), 6.75-6.18 (m, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe resulting solid was collected

Sources & evidence

ORD record
ord-effe65fdbc794a7baab609aa4736f552
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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