4-Aminophenol → HCID 54909083, compound

HRID 1932437Notes

Reaction equation

HRID 1932437 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1>CO>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)=[N:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 54909083HCID 54909083, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of sodium hydroxide (730 mg, 18.25 mmol) in methanol was added 4-aminophenol (2.00 g, 18.32 mmol). After the resulting mixture was made to dissolve, methanol was evaporated under reduced pressure. To the residue was added DMF (20 mL), and then 2-chloro-5-nitropyridine (2.91 g, 18.35 mmol). The reaction solution was stirred for 1.5 hours at 70° C., and then concentrated under reduced pressure. Water was added to the residue, and the resulting solution was extracted with ethyl acetate. The ethyl acetate layer was washed with brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, after which solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to thereby yield 3.37 g of the title compound.

Workup

  1. dissolutionto dissolve
  2. custommethanol was evaporated under reduced pressure
  3. additionTo the residue was added DMF (20 mL)
  4. concentrationconcentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe resulting solution was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with brine
  8. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  9. customafter which solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a79fd0cf38a64bdea3347c503fc49f3a
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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