Sodium Hydroxide → 3-(1,2-Dihydro-1-oxo-7-isoquinolinyl)-benzonitrile

HRID 479563ノート

反応式

HRID 479563 の反応式
[OH-].[Na+].[C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)#[N:4].Br[C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][NH:21][C:22]2=[O:25])=[CH:17][CH:16]=1>O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][NH:21][C:22]3=[O:25])=[CH:17][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)#[N:4]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 27343253-Cyanophenylboronic acidHCID 112761337-Bromoisoquinolin-1-ol

生成物 1

HCID 534249783-(1,2-Dihydro-1-oxo-7-isoquinolinyl)-benzonitrile収率 99.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of sodium hydroxide (214 g, 5.35 mol) in water (10 L) was added to a stirred suspension of 3-cyanophenylboronic acid (24% water content, 1.13 kg, 5.8 mol) and 7-bromoisoquinolinone (1.0 kg, 4.46 mol) in methanol (10 L) and the mixture stirred for 1 hour. Palladium acetate (10 g, 44.5 mmol) was added and the mixture was heated at reflux under N2 for 5 hours and then cooled to room temperature and stirred overnight. The light grey solid was collected by filtration. The damp solid was reslurried in water (10 L) and heated to 80° C. for 30 minutes. The mixture was then cooled to room temperature and the solid collected by filtration, washed with water (2 L) then methanol (2 L) and dried in vacuo at 50° C. to give 7-(3-cyanophenyl)isoquinolinone (1.09 kg, 4.43 mol, 99%) as a light grey solid.

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux under N2 for 5 hours
  3. stirringstirred overnight
  4. filtrationThe light grey solid was collected by filtration
  5. temperatureheated to 80° C. for 30 minutes
  6. temperatureThe mixture was then cooled to room temperature
  7. filtrationthe solid collected by filtration
  8. washwashed with water (2 L)
  9. dry with materialmethanol (2 L) and dried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-12a5179f31154c14bfb5d270d60238e3
出典データセット
uspto-grants-2003_11
特許番号
US06645979B2

反応ノート

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