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

HRID 635004Notes

Reaction equation

HRID 635004 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-8e4dafbb9f4a47688a1ce6bfedfa954e
Source dataset
uspto-grants-2001_02
Patent number
US06184237B2

Reaction notes

Loading…