HCID 59452704, compound → 2-(Ethyloxy)-4-(4-pyridinyl)aniline

HRID 419562Notes

Reaction equation

HRID 419562 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CCOC(C)=O.CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[NH2:10])[CH3:2]

Participants

3

Reactant 1

HCID 59452704HCID 59452704, compound

Product 1

HCID 594527332-(Ethyloxy)-4-(4-pyridinyl)anilineYield 83.4%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

4-[3-(Ethyloxy)-4-nitrophenyl]pyridine (3.57 g, 14.62 mmol) was place in a 250 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (2.85 g, 0.73 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 6 hours. 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 C (2.62 g, 12.2 mmol, 83%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.44-8.48 (m, 2H), 7.57 (dd, J=4.58, 1.46 Hz, 2H), 7.16-7.21 (m, 2H), 6.70 (d, J=7.87 Hz, 1H), 5.09 (bs, 2H), 4.09 (q, J=6.96 Hz, 2H), 1.34 (t, J=6.96 Hz, 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-3625bb46d158416c95a95ac392126099
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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