4-Aminophenol → HCID 57541500, compound

HRID 1522919Notes

Reaction equation

HRID 1522919 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.CC(C)([O-])C.[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[NH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=2)=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 11430Potassium CarbonateHCID 11806045tert-Butyl 4-chloropicolinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 57541500HCID 57541500, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, p-aminophenol (0.51 g, 4.70 mmol, 1 eq) was dissolved in N,N-dimethylformamide (10 mL). To the resulted solution, potassium tert-butoxide (0.53 g, 4.70 mmol, 1 eq) was added in portions and the resulted mixture was stirred for 0.5 hours. Tert-butyl 4-chloropicolinate (1 g, 4.70 mmol, 1 eq) and potassium carbonate (45 mg, 0.33 mmol, 0.07 eq) were added, and the mixture was heated to 80° C. and stirred for 2 hours. The mixture was cooled to room temperature and ethyl acetate (50 mL) was added. The mixture was filtered to remove the undissolved material and the filtrate was washed with saturated brine (20 mL×2). The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent. The residue was purified by column chromatography (dichloromethane:ethyl acetate=30:1) to give the title compound (805 mg, purity 96%, yield 60%).

Workup

  1. stirringstirred for 2 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe mixture was filtered
  4. customto remove the undissolved material
  5. washthe filtrate was washed with saturated brine (20 mL×2)
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by column chromatography (dichloromethane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-9939d6ac1b1f415b824086b9150f9eca
Source dataset
uspto-grants-2015_07
Patent number
US09078933B2

Reaction notes

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