3-(4-Nitrophenyl)pyridine → 4-(Pyridin-3-yl)aniline

HRID 1279931

反応式

HRID 1279931 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

参加物

3

反応物 1

HCID 2315043-(4-Nitrophenyl)pyridine

生成物 1

HCID 4595224-(Pyridin-3-yl)aniline収率 95%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

In a flame-dried r.b. flask equipped with a magnetic stirring bar was dissolved 3-(4-nitrophenyl)pyridine (131 mg, 0.655 mmol) and 10% Pd on C (10 mg) in anhydrous CH2C12 (3 mL) was added. The flask was repeatedly evacuated and filled with N2 to remove any residual O2, and then H2 gas was introduced. The solution was stirred at rt for 18 h, filtered though a Celite™ plug and concentrated int vacuo to give the desired amine (105 mg, 95%) as an off-white solid. Data for 3-(4-aminophenyl)pyridine: Rf=0.17 (silica gel, methanol/CHCl3, 5/95); 1H NMR (400 MHz, acetone-d6) 8.77 (d, J=2.3, 1H), 8.42 (dd, J=6.4, 1.6, 1H), 7.88 (m, 1H), 7.41 (d, J=8.5, 2H), 7.33 (m, 1H), 6.78 (d, J=8.5, 2H), 4.86 (br s, 2H).

後処理

  1. customflask equipped with a magnetic stirring bar
  2. additionwas added
  3. customThe flask was repeatedly evacuated
  4. additionfilled with N2
  5. customto remove any residual O2
  6. additionH2 gas was introduced
  7. filtrationfiltered though a Celite™ plug
  8. concentrationconcentrated int vacuo

出典と根拠

ORDレコード
ord-880d2bcc296a4d0eb606cf4f8c3f457b
出典データセット
uspto-grants-2002_09
特許番号
US06448405B1

関連ノート

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