4-(3-Methoxy-4-nitrophenyl)pyridine → 2-(Methyloxy)-4-(4-piperidinyl)aniline

HRID 419558ノート

反応式

HRID 419558 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CC(O)=O.CC(O)C.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

参加物

5

反応物 1

HCID 137288334-(3-Methoxy-4-nitrophenyl)pyridine

生成物 1

HCID 594529072-(Methyloxy)-4-(4-piperidinyl)aniline収率 12%

試薬・触媒・溶媒 3

HCID 82844Platinum oxide (PtO)触媒HCID 176Acetic Acid溶媒HCID 3776Isopropanol溶媒2 回

実験手順

To 4-[3-(methyloxy)-4-nitrophenyl]pyridine (Example 137, step A) (4.6 g, 20 mmol) in HOAc (20 mL) is added platinum oxide (460 mg, 2 mmol). The reaction was evacuated then refilled with 60 psi H2 gas. The reaction was stirred under a H2 atmosphere for 3 days. The reaction was evacuated and the atmosphere replaced with N2. The solvent was removed under vacuum, and the residue taken up in DCM/MeOH. Silica was added, and the solvent removed under vacuum. Silica gel chromatography provided material which contained product and other impurities. This material was dissolved in iPrOH and allowed to stand overnight. The crystals which formed were collected by decanting off the solvent and rinsing with iPrOH. Obtained the title compound of step A (500 mg, 2.4 mmol, 12%) slightly wet with iPrOH as colorless crystals. 1H NMR (400 MHz, DMSO-d6) δ 6.68-6.60 (m, 3H), 3.83 (s, 3H), 3.71 (br s, 2H), 3.38-3.31 (m, 2H), 2.85-2.75 (m, 2H), 2.59-2.49 (m, 1H), 1.91-1.75 (m, 5H).

後処理

  1. customThe reaction was evacuated
  2. additionthen refilled with 60 psi H2 gas
  3. customThe reaction was evacuated
  4. customThe solvent was removed under vacuum
  5. additionSilica was added
  6. customthe solvent removed under vacuum
  7. customSilica gel chromatography provided material which
  8. waitto stand overnight
  9. customThe crystals which formed
  10. customwere collected
  11. customby decanting off the solvent
  12. washrinsing with iPrOH

出典と根拠

ORDレコード
ord-95dc5de5cae743668b3eb387e017d351
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…