Sodium Iodide → 3-(3-Methyl-1-oxo-1,2-dihydroisoquinolin-4-yl)benzonitrile

HRID 1921330Notes

Reaction equation

HRID 1921330 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19]C)=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[I-].[Na+].Cl[Si](C)(C)[CH3:25]>C(#N)C.O>[CH3:25][C:10]1[NH:11][C:12](=[O:19])[C:13]2[C:18]([C:9]=1[C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 674925834-(3-Cyanophenyl)-1-methoxyisoquinoline

Product 1

HCID 116945723-(3-Methyl-1-oxo-1,2-dihydroisoquinolin-4-yl)benzonitrileYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3-cyanophenyl)-1-methoxyisoquinoline (200 mg, 0.73 mmol) in acetonitrile (6 mL) is added sodium iodide (219 mg, 1.46 mmol) followed by chlorotrimethylsilane (186 μL, 1.46 mmol) and the mixture is heated at reflux for 1.5 hr. The cooled reaction is diluted with water (15 mL) and the solids are collected by filtration, washed with water and dried to give 3-(3-methyl-1-oxo-1,2-dihydroisoquinolin-4-yl)benzonitrile (157 mg, 83% yield). 1H NMR (δ ppm) 11.55 (1H, s), 8.22 (1H, d), 7.95 (1H, d), 7.82 (1H, s), 7.72 (1H, t), 7.66 (1H, m), 7.60 (1H, m), 7.47 (1H, t), 6.94 (1H, d), 1.99 (3H, s).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1.5 hr
  3. customThe cooled reaction
  4. filtrationthe solids are collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4fb519fc587f4eddbafb76a6c0d55d72
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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