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

HRID 479563노트

반응식

HRID 479563 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-12a5179f31154c14bfb5d270d60238e3
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645979B2

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