Iodine → 5-Chloro-7-iodo-2-methyl-8-quinolinol

HRID 2301440Notes

Reaction equation

HRID 2301440 reaction equation
[I:1]I.[Cl:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH3:15])=[N:9]2.ICl>CO>[Cl:3][C:4]1[CH:13]=[C:12]([I:1])[C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH3:15])=[N:9]2

Participants

5

Reactant 3

HCID 807IodineHCID 24640Iodine chlorideHCID 129451955-Chloro-2-methylquinolin-8-ol

Product 1

HCID 183725885-Chloro-7-iodo-2-methyl-8-quinolinol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodine monchloride (19.0 g) is added to a solution of 5-chloro-8-hydroxy-2-methylquinoline (21.5 g) in 250 mL of MeOH, and the resulting mixture is stirred for 3 h. Additional iodine monochloride (4.5 g) is then added, and the mixture is stirred for another 18 h. The reaction mixture is quenched with sat'd Na2SO3 (aq), then neutralized with sat'd NaHCO3 (aq). The solid precipitate is collected by filtration and dried under vacuum to give 31.22 g of the title compound as a pale green solid.

Workup

  1. stirringthe mixture is stirred for another 18 h
  2. customThe reaction mixture is quenched with sat'd Na2SO3 (aq)
  3. filtrationThe solid precipitate is collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-896684ac7e214d35aca1ec85991a4169
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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