Hydrochloric Acid → HCID 4197917, compound

HRID 240341Notes

Reaction equation

HRID 240341 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[CH3:12][O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.Cl>C(OCCO)C>[CH3:12][O:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7732P-AnisidineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 4197917HCID 4197917, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

5.0 g (32 mmol) of 2-chloro-3-nitropyridine was dissolved in 2-ethoxyethanol (150 mL), and water (150 mL) was added thereto. To the mixed solution, 3.9 g (32 mmol) of 4-methoxyaniline and 6 N hydrochloric acid (1 mL) were added, and the mixture was heated to reflux for 12 hours while stirring. After confirming the completion of the reaction, the reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and washed with saturated brine, and then the obtained organic layer was dried over anhydrous magnesium sulfate. The inorganic matter was separated by filtration, and then the solvent was distilled off under reduced pressure, to obtain 6.6 g (yield: 85%) of N-(4-methoxyphenyl)-3-nitropyridin-2-amine as orange-colored crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 12 hours
  3. customthe completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  8. customThe inorganic matter was separated by filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-59d19ddbe8804d43ae9c7749f1408eeb
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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