Ethyl Acetate → 5-Amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine

HRID 2395696Notes

Reaction equation

HRID 2395696 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][N:17]=1.C(OCC)(=O)C>[C].[Pd].CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 110673292-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy)-5-nitropyridine

Product 1

HCID 110877225-Amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridineYield 93.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-nitropyridine (13.4 g), palladium-carbon (5%, 1.5 g), ethyl acetate (200 ml), and methanol (150 ml) was catalytically reduced at room temperature at 1 atm. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residual crystal was collected by filtration and recrystallized from ethyl acetate-hexane to yield 5-amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (11.4 g, 93%) as a brown crystal.

Workup

  1. customwas catalytically reduced at room temperature at 1 atm
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. filtrationthe resulting residual crystal was collected by filtration
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8d4e5c2bcfcb46eb84f4622815ce113c
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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