4-Methoxyphenol → HCID 2728288, compound

HRID 1379657Notes

Reaction equation

HRID 1379657 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[K+].Cl[C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][N:14]=1>CO.C1(C)C=CC=CC=1>[NH2:19][C:18]1[C:13]([O:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 2728288HCID 2728288, compoundYield 108.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

5.87 g of 4-methoxyphenol were dissolved in 8 ml of methanol; 2.61 g of KOH were added, the whole was stirred for 2 hours, and the solvent was evaporated. The solid obtained was dissolved in 150 ml of anhydrous toluene. With stirring, 5 g of 2-chloro-3-nitropyridine were added at 70°-80° C. in the course of 4 hours under a nitrogen atmosphere. The whole was then stirred at ambient temperature for 2 hours. It was washed with 10% aqueous NaOH and then with plenty of water. The organic phase was treated with active carbon at room temperature for 60 minutes. It was filtered and the filtrate was dried with anhydrous magnesium sulphate. After evaporation of the solvent at low pressure, 7.4 g of 3-amino-2-(4-methoxyphenoxy)pyridine (95% yield) were obtained as a pale yellow solid which melted at 105°-107° C. with decomposition.

Workup

  1. customthe solvent was evaporated
  2. customThe solid obtained
  3. stirringWith stirring
  4. stirringThe whole was then stirred at ambient temperature for 2 hours
  5. washIt was washed with 10% aqueous NaOH
  6. additionThe organic phase was treated with active carbon at room temperature for 60 minutes
  7. filtrationIt was filtered
  8. dry with materialthe filtrate was dried with anhydrous magnesium sulphate
  9. customAfter evaporation of the solvent at low pressure

Sources & evidence

ORD record
ord-731bbb3dae174181a561ea87ebe7fadf
Source dataset
uspto-grants-1997_09
Patent number
US05672613

Reaction notes

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