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

HRID 419531ノート

反応式

HRID 419531 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21584119Ethylacetate methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08d45c43c21d4205a44ccf57f38ee451
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

読み込み中…