Hydrochloric Acid → Methyl 3-[(5-aminopyridin-2-yl)oxy]-4-methoxybenzoate

HRID 1800431Notes

Reaction equation

HRID 1800431 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=1.Cl>C(O)C.[Fe]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[C:7]([O:9][CH3:10])=[O:8])=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68418010Methyl 4-methoxy-3-[(5-nitropyridin-2-yl)oxy]benzoate

Product 1

HCID 68417783Methyl 3-[(5-aminopyridin-2-yl)oxy]-4-methoxybenzoateYield 109.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 4-methoxy-3-[(5-nitropyridin-2-yl)oxy]benzoate (26.7 mmol) in ethanol (250 mL) were added iron powder (5.6 g, 0.1 mol) and 6N hydrochloric acid (50 mL) with heating under reflux and vigorous stirring, and the mixture was vigorously stirred under refluxing condition for 1.5 hr. The reaction solution was filtered through celite, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate (350 mL), and washed with 1N aqueous sodium hydroxide solution (200 mL×2). The aqueous layer was extracted with ethyl acetate (150 mL×3), and the combined organic layer was washed with saturated aqueous ammonium chloride solution (100 mL×2), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (8.0 g) as a brownish-red syrup substance.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureunder refluxing condition for 1.5 hr
  4. filtrationThe reaction solution was filtered through celite
  5. filtrationthe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionThe residue was diluted with ethyl acetate (350 mL)
  8. washwashed with 1N aqueous sodium hydroxide solution (200 mL×2)
  9. extractionThe aqueous layer was extracted with ethyl acetate (150 mL×3)
  10. washthe combined organic layer was washed with saturated aqueous ammonium chloride solution (100 mL×2)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationThe insoluble material was filtered off
  13. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-adc273a6e66843f3a23136b4aa02c592
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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