Nitric Acid → 4-Fluoro-2-methyl-5-nitroaniline

HRID 599335

Reaction equation

HRID 599335 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1>OS(O)(=O)=O>[F:5][C:6]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 679824-Fluoro-2-methylaniline

Product 1

HCID 190352714-Fluoro-2-methyl-5-nitroanilineYield 74%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

Concentrated nitric acid (17 g, 0.18 mol) was added dropwise to a stirred solution of 4-fluoro-2-methylaniline (20 g, 0.16 mol) in cone H2SO4 (300 mL) at −10° C. The mixture was stirred at −10° C. for 10 min., and the reaction mixture was poured into ice water. The resultant solid was collected by filtration and partitioned between EtOAc and aq Na2CO3 solution (pH 8). The organic solution was washed with brine, dried (MgSO4) and concentrated to give 4-fluoro-2-methyl-5-nitroaniline (20 g, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.27 (d, J=6.8 Hz, 1 H), 7.14 (d, J=12.4 Hz, 1 H) 5.37 (s, 2 H), 2.10 (s, 3 H).

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. custompartitioned between EtOAc and aq Na2CO3 solution (pH 8)
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d38e53abfed40418e574501f432404f
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Linked notes

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