Hydrochloric Acid → 4-Fluoro-2-methyl-6-nitroaniline

HRID 2203208Notes

Reaction equation

HRID 2203208 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11]C(=O)C)=[C:4]([CH3:15])[CH:3]=1.Cl>O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH2:11])=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54330341N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

Product 1

HCID 103748424-Fluoro-2-methyl-6-nitroanilineYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide (20 g, crude), concentrated hydrochloric acid (100 mL), and H2O (100 mL) was refluxed overnight. The reaction mixture was subsequently extracted with DCM. The organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer was >7. The organic phase was washed with water and dried over Na2SO4. The solvent was evaporated to give the title compound as a solid (5.5 g, 34%). 1H NMR (400 MHz, CDCl3) δ ppm 7.68 (1H, dd, J1=2.8 Hz, J2=9.2 Hz), 7.05 (1H, dd, J1=2.8 Hz, J2=8.0 Hz), 5.99 (2H, s), 2.19 (3H, s).

Workup

  1. temperaturewas refluxed overnight
  2. extractionThe reaction mixture was subsequently extracted with DCM
  3. washThe organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer
  4. washThe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-99b2bf32e22d4909bc05264da8cdccdc
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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