Dichloromethane → 3-(Pyridin-3-yloxy)aniline

HRID 2231741ノート

反応式

HRID 2231741 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([N+:14]([O-])=O)[CH:11]=[CH:12][CH:13]=2)[CH:2]=1.C(Cl)Cl>O.[Fe]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[NH2:14])[CH:2]=1

参加物

5

反応物 2

HCID 6344DichloromethaneHCID 212855723-(3-Nitrophenoxy)pyridine

生成物 1

HCID 212855823-(Pyridin-3-yloxy)aniline

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

The 3-(3-pyridyloxy)aniline is prepared as follows: ferric chloride (0.4 g) is added, at a temperature between 90° and 98° C., to a suspension of 3-(3-pyridyloxy)nitrobenzene (16.2 g) and iron powder (37.5 g) in distilled water (40 cc) which is heated to a temperature in the vicinity of 90° C. The suspension obtained is heated at a temperature in the vicinity of 98° C. for 1 hour and 15 minutes and then stirred at a temperature in the vicinity of 20° C. for 16 hours, treated with methylene chloride (550 cc) and distilled water (75 cc) and filtered. The organic phase is separated, dried over anhydrous magnesium sulphate, treated with decolourizing charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. A crude oil (13.1 g) is thereby obtained which is chromatographed on a 6 cm diameter column containing silica (0.02-0.045 mm; 450 g). Elution is carried out with mixtures of ethyl acetate and cyclohexane at a pressure of 0.4 bar (40 kPa), collecting 150 cc fractions. The first 15 fractions originating from elution with an ethyl acetate:cyclohexane (50:50 by volume) mixture are discarded. The following 5 fractions originating from elution with an ethyl acetate:cyclohexane (50:50 by volume) mixture and the following 5 fractions originating from elution with pure ethyl acetate are combined and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. 3-(3-pyridyloxy)aniline in the form of an orange-yellow liquid [Rf=0.25; silica gel thin layer chromatography; eluant: cyclohexane:ethyl acetate (50:50 by volume)] is thereby obtained.

後処理

  1. customThe suspension obtained
  2. temperatureis heated at a temperature in the vicinity of 98° C. for 1 hour and 15 minutes
  3. distillationdistilled water (75 cc)
  4. filtrationfiltered
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous magnesium sulphate
  7. additiontreated with decolourizing charcoal (0.5 g)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  10. customA crude oil (13.1 g) is thereby obtained which

出典と根拠

ORDレコード
ord-26384c3f89bc4335b5b16bb49f9982de
出典データセット
uspto-grants-1988_11
特許番号
US04783472

反応ノート

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