Sodium Cyanide → 6-Hydroxy-3-quinolinecarbonitrile

HRID 2222302ノート

反応式

HRID 2222302 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.[C-:13]#[N:14].[Na+].[Cl-].[NH4+]>CN1CCCC1=O.O>[C:13]([C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2)#[N:14]

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 148078713-Bromoquinolin-6-ol

生成物 1

HCID 219231416-Hydroxy-3-quinolinecarbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

3-Bromo-6-hydroxyquinoline (1.12 g) in dry N-methylpyrrolidin-2-one (10 ml) was treated with cuprous cyanide (0.55 g) and stirred at 150° C. for 7 hours under an atmosphere of nitrogen then stored at ambient temperature for 18 hours. The mixture was treated with sodium cyanide (1.5 g) in water (5 ml) and heated at 75° C. for 15 minutes. 10% Aqueous ammonium chloride solution (25 ml) was added and the mixture cooled to ambient temperature. The reaction mixture was extracted with ethyl acetate and the organic phase separated, washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give a yellow brown solid. The solid was fractionated by chromatography to give the required product as a yellow solid.

後処理

  1. waitthen stored at ambient temperature for 18 hours
  2. temperatureheated at 75° C. for 15 minutes
  3. temperaturethe mixture cooled to ambient temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. customthe organic phase separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a yellow brown solid

出典と根拠

ORDレコード
ord-9eede1a3f0ff474aab195bf000d3a205
出典データセット
uspto-grants-2008_05
特許番号
US07371764B2

反応ノート

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