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

HRID 741837Notes

Reaction equation

HRID 741837 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) (Aldrich) 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, brine, dried (Na2SO4) and concentrated providing the title compound which 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, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-035d1e65fde54f2ea900ce1870d4af21
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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