Iodine → HCID 59575322, compound

HRID 1468596Notes

Reaction equation

HRID 1468596 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH3:14])[CH:8]=1.II>C1(C)C=CC=CC=1>[CH3:14][O:13][C:9]1[N:10]=[CH:11][C:12]2[C:7]([CH:8]=1)=[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]1=[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=21

Participants

4

Reactant 2

HCID 807IodineHCID 59575353HCID 59575353, compound

Product 1

HCID 59575322HCID 59575322, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(biphenyl-2-yl)-2-methoxypyridine (2.9 g, 10.9 mmol), iodine (281 mg, 1.1 mmol) and toluene were charged into a double-walled quartz photochemical reactor equipped with magnetic stirring, an air bubbler and an ultraviolet lamp. Gentle air was bubbled through the solvent while it was irradiated for 15 h. The reaction mixture was purified by flash chromatography on silica (hexane:ethyl acetate) and sonicated in MeOH to give 3-methoxydibenzo[f,h]isoquinoline (0.5 g, 17%).

Workup

  1. customequipped with magnetic stirring
  2. customGentle air was bubbled through the solvent while it
  3. customwas irradiated for 15 h
  4. customThe reaction mixture was purified by flash chromatography on silica (hexane:ethyl acetate)
  5. customsonicated in MeOH

Sources & evidence

ORD record
ord-b231ddf65ed342c78cee04f37d31cd62
Source dataset
uspto-grants-2015_04
Patent number
US09005771B2

Reaction notes

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