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

HRID 382890Notes

Reaction equation

HRID 382890 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 sated Na2SO3 (aq), then neutralized with sat'd NaHCO, (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 sated Na2SO3 (aq)
  3. filtrationThe solid precipitate is collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-91aa603a2c9f464780627d350d438898
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Reaction notes

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