3-(2-Chloro-4-nitrophenyl)-4-methylpyridine → 3-Chloro-4-(4-methylpyridin-3-yl)aniline

HRID 1405078Notes

Reaction equation

HRID 1405078 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[CH3:17]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[CH3:17])[NH2:8]

Participants

4

Reactant 1

HCID 667148853-(2-Chloro-4-nitrophenyl)-4-methylpyridine

Product 1

HCID 667144823-Chloro-4-(4-methylpyridin-3-yl)anilineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 27A (0.136 g, 0.547 mmol) in EtOAc (2.73 mL) was added Pd/C (0.058 g, 0.055 mmol). The mixture was placed under an atmosphere of H2 for 18 hours. The reaction mixture was filtered through CELITE® and the filter cake was washed with CH2Cl2. The solvent was evaporated and the crude material re-dissolved in a minimal amount of CH2Cl2 and chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (40 g column, 1-20% MeOH in CH2Cl2 over 25 min) gave the title compound (0.106 g, 0.485 mmol, 89% yield) as an orange residue. HPLC Ret timej:1.06 min. MS (ES): m/z=219.1 [M+H]+. Intermediate 27 was used in the synthesis of Example 178.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. washthe filter cake was washed with CH2Cl2
  3. customThe solvent was evaporated
  4. dissolutionthe crude material re-dissolved in a minimal amount of CH2Cl2
  5. customchromatographed
  6. customPurification of the crude material by silica gel chromatography
  7. customan ISCO machine (40 g column, 1-20% MeOH in CH2Cl2 over 25 min)

Sources & evidence

ORD record
ord-31bb545b8a6d47e7a00ee78aba51279a
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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