Ethanol → (4-Amino-3-ethoxyphenyl)(2-pyridyl)methanol

HRID 856745Notes

Reaction equation

HRID 856745 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[OH:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2].C(OCC)(=O)C.C(O)C>C(O)(=O)C>[NH2:10][C:9]1[CH:8]=[CH:7][C:6]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[OH:14])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 22938745(3-Ethoxy-4-nitrophenyl)(2-pyridyl)methanol

Product 1

HCID 22938366(4-Amino-3-ethoxyphenyl)(2-pyridyl)methanolYield 15.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (3-ethoxy-4-nitrophenyl)(2-pyridyl)methanol (2.5 g) in acetic acid (50 ml), reduced iron (7.5 g) was added to the mixture and the mixture was stirred overnight. Ethyl acetate and ethanol were added to the mixture, and the unnecessary substances were filtered off. The filtrate was concentrated under reduced pressure, the residue was diluted with ethyl acetate and neutralized with an aqueous solution of saturated sodium bicarbonate. The organic layer was separated and washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) and recrystallized from hexane-ethyl acetate, to give (4-amino-3-ethoxyphenyl)(2-pyridyl)methanol (340 mg) as crystals.

Workup

  1. filtrationthe unnecessary substances were filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2)
  9. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8169bdccb3c041fcaa44015a14a4478a
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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