Methanol → 5-Fluoro-3-methyl-2-nitroaniline

HRID 1767016Notes

Reaction equation

HRID 1767016 reaction equation
[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH2:9]C(O)=O)[CH:5]=[C:6]([F:8])[CH:7]=1.CO>C(#N)C>[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 887MethanolHCID 235416553-Amino-5-fluoro-2-nitro phenyl acetic acid

Product 1

HCID 220210255-Fluoro-3-methyl-2-nitroanilineYield 103.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the crude 3-Amino-5-fluoro-2-nitro phenyl acetic acid (3.6 g, 16.8 mmol) was added Cu2O (10.1 g, 70.6 mmol) in 120 mL of acetonitrile along with 50 uL of methanol and the suspension was refluxed for 12 hours. The reaction mixture was filtered through Celite and the Celite pad washed with water and ethyl acetate. The filtrate was extracted with ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to give 2.95 g of material which by 1H NMR was 80% pure. ESIMS [M+Na]−193; 1H NMR (500 MHz, DMSO) δ 6.67 (s, 2H), 6.56 (dd, J=11, 2.8 Hz, 1H), 6.39 (dd, J=11, 2.8 Hz, 1H), 2.50 (s, 3H).

Workup

  1. temperaturethe suspension was refluxed for 12 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe Celite pad washed with water and ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f3a2b4e835c242eeaaf6eaed4b7b8def
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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