2-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-nitropyridine → 2-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-amino-pyridine

HRID 377103

Reaction equation

HRID 377103 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][N:8]=2)=[C:4]([CH3:19])[CH:3]=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[C:12]([CH3:13])=[CH:11][C:10]([NH2:14])=[CH:9][N:8]=2)=[C:4]([CH3:19])[CH:3]=1

Participants

5

Reactant 2

HCID 184194612-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 158876162-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-amino-pyridine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2- (4-chloro-2-methyl-phenoxy) -3-methyl-5-nitropyridine (5.8 g, 20.8 mmol) was dissolved in 95% ethanol (50 mL) and treated with 20% palladium hydroxide on carbon (350 mg). The reaction mixture was shaken in a hydrogen atmosphere (40 psi) for 1 hour. The solution was filtered through celite and concentrated in vacuo followed by chromatography on SiO2 using 1:1 ethyl acetate/hexanes as eluant. MS (m/z): 248/250 (M+H)+ ; C13H13N2OCl requires 248.7.

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28a4d5393c8e4226b3b0cf1e9d761342
Source dataset
uspto-grants-2000_02
Patent number
US06022884

Linked notes

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