Sodium Hydroxide → 4-(5-Hydroxypyridin-3-yl)benzonitrile

HRID 1685404ノート

反応式

HRID 1685404 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH:6]=[N:7][CH:8]=1.Cl.[NH+]1C=CC=CC=1.[OH-].[Na+]>O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH:6]=[N:7][CH:8]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21584435Pyridinium hydrochlorideHCID 672914774-(5-Methoxy-3-pyridinyl)benzonitrile

生成物 1

HCID 532175154-(5-Hydroxypyridin-3-yl)benzonitrile収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A mixture of 1.9 g (9.02 mM) of 4-(5-methoxy-3-pyridinyl)benzonitrile and 6.39 g (54.2 mM) of pyridinium hydrochloride is heated at 160° C. for 5 hours. After cooling and the addition of water, the pH is adjusted to 5 with concentrated sodium hydroxide solution. The mixture is extracted with ethyl acetate and the extract is dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate 92/8; v/v, then dichloromethane/methanol 9/1; v/v) to give the expected product in the form of a beige solid with a yield of 76%.

後処理

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe extract is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe evaporation residue is purified by chromatography on a silica column (eluent

出典と根拠

ORDレコード
ord-87ed16d436274bd0ae60be52cb000c08
出典データセット
uspto-grants-2012_04
特許番号
US08148407B2

反応ノート

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