Hydrochloric Acid → N-(3-fluoro-4-methylphenyl)-3-nitro-2-pyridylamine

HRID 240363

Reaction equation

HRID 240363 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[CH3:19])[NH2:15].Cl.O>C(OCCO)C>[F:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 99573-Fluoro-4-methylanilineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 40676958N-(3-fluoro-4-methylphenyl)-3-nitro-2-pyridylamineYield 82,342.5%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

45 g (0.28 mmol) of 2-chloro-3-nitropyridine was dissolved in 2-ethoxyethanol (300 ml), and 36 g (0.28 mmol) of 3-fluoro-4-methylaniline, 12N-hydrochloric acid and water (300 ml) were added thereto. Mixed solution was heated to reflux for 24 hours while stirring. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The solution was extracted with ethyl acetate, and washed with saturated brine, and then the obtained organic layer was dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and the residue thus obtained was washed with diisopropyl ether to obtain 57 g (yield: 82%) of N-(3-fluoro-4-methylphenyl)-3-nitro-2-pyridylamine.

Workup

  1. temperatureMixed solution was heated
  2. temperatureto reflux for 24 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThe solution was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  7. concentrationThe mixture was concentrated under reduced pressure
  8. customthe residue thus obtained
  9. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-9fbcc228a5194e8cae52bfc3ab30a05f
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Linked notes

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