4-Nitrophenol → 4-(4-Nitrophenoxy)pyridin-2-amine

HRID 492745Notes

Reaction equation

HRID 492745 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[NH2:1][C:2]1[CH:7]=[C:6]([O:18][C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 81531DiisopropylethylamineHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 229367164-(4-Nitrophenoxy)pyridin-2-amineYield 21.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

2-Amino-4-chloropyridine (2.00 g) was dissolved in N-methylpyrrolidone (31.8 ml), and then 4-nitrophenol (6.51 g) and N,N-diisopropylethylamine (15.9 ml) were added thereto under a nitrogen atmosphere, followed by stirring at 150° C. for 3 days. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and a 1 N aqueous solution of sodium hydroxide (32 ml). The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2 to 1:5). Fractions containing the target compound were concentrated under a reduced pressure to give a residue, which was then dried in vacuum to provide the titled compound (764 mg, 21.2%) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. custompartitioned between ethyl acetate
  3. washThe organic layer was washed with water and brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2 to 1:5)
  8. additionFractions containing the target compound
  9. concentrationwere concentrated under a reduced pressure
  10. customto give a residue, which
  11. customwas then dried in vacuum

Sources & evidence

ORD record
ord-3f2cedb04bb94a7ebc4f4fd3a9261205
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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