4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]pyridine → 5-Methyl-2-(methyloxy)-4-(4-pyridinyl)aniline

HRID 419531Notes

Reaction equation

HRID 419531 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1>CCOC(C)=O.CO>[CH3:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

Participants

3

Reactant 1

HCID 594526494-[2-Methyl-5-(methyloxy)-4-nitrophenyl]pyridine

Product 1

HCID 594527995-Methyl-2-(methyloxy)-4-(4-pyridinyl)anilineYield 106.1%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

4-[2-methyl-5-(methyloxy)-4-nitrophenyl]pyridine (Example 157, step A) (2.44 g, 9.99 mmol) was placed in a 250 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (1.17 g, 0.3 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (60 psi). The solution stirred for 72 h. The vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to give the title compound of step A (2.28 g, 10.6 mmol, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.50-8.53 (m, 2H), 7.30-7.33 (m, 2H), 6.68 (s, 1H), 6.54 (s, 1H), 4.88 (bs, 2H), 3.75 (s, 3H), 2.12 (s, 3H).

Workup

  1. customThe flask was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove any H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

Sources & evidence

ORD record
ord-08d45c43c21d4205a44ccf57f38ee451
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…