4,7-Dichloroquinoline → 7-Chloro-4-iodoquinoline

HRID 1901120Notes

Reaction equation

HRID 1901120 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[IH:13].[OH-].[Na+]>>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([I:13])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 68664,7-DichloroquinolineHCID 14798Sodium HydroxideHCID 24841Hydrogen iodide

Product 1

HCID 111853697-Chloro-4-iodoquinoline

Conditions

Temperature
130 °C

Procedure

4,7-Dichloroquinoline (50 g) was added, in small portions, to HI (425 mL) at r.t. and then heated at 130° C. for 5 h. The mixture was cooled, poured into ice/H2O (600 mL), made basic (pH 10) with 10N NaOH, and extracted with CHCl3. The combined organics were washed with NH4OAc buffer, 10% Na2S2O3 and brine. Drying (Na2SO4) and concentration provided the title compound that was used as such.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with CHCl3
  3. washThe combined organics were washed with NH4OAc buffer, 10% Na2S2O3 and brine
  4. customDrying
  5. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-c691830c792f43faa3d9b362a4530a5a
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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