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

HRID 479563Notes

Reaction equation

HRID 479563 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-12a5179f31154c14bfb5d270d60238e3
Source dataset
uspto-grants-2003_11
Patent number
US06645979B2

Reaction notes

Loading…