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

HRID 1267313

Reaction equation

HRID 1267313 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) and ethyl acetate (200 ml)-methanol (150 ml) was subjected catalytic hydrogenation at room temperature under one atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residual crystals were collected by filtration to obtain 5-amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (11.4 g, 93%). Recrystallization from ethyl acetate-hexane gave brown crystals, m.p.107.0-108.0° C.

Workup

  1. customat room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. filtrationThe residual crystals were collected by filtration

Sources & evidence

ORD record
ord-0c1aaefdf7914842988a2268d63fd681
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Linked notes

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