Ammonia → 3-Iodoquinolin-6-ol

HRID 2091465Notes

Reaction equation

HRID 2091465 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.[I-:13].[Na+].N.Cl>O1CCOCC1.[Cu](I)I>[I:13][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 148078713-Bromoquinolin-6-ol

Product 1

HCID 574180403-Iodoquinolin-6-ol

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 3-bromo-6-hydroxyquinoline (preparation described in Liebigs Ann Chem 1966, 98-106), (3.0 g), sodium iodide (4.0 g) and copper iodide (0.25 g) in dioxane (19.5 ml) is added N,N′-tetramethyl-ethane-1,2-diamine (0.24 g) in a sealed tube under argon. The mixture is stirred at 120° C. for 14 h and upon cooling is treated with aqueous ammonia followed by aqueous hydrochloric acid to reach pH 5. Extraction with ethyl acetate, drying of the organic phase over magnesium sulphate, filtration and evaporation under reduced pressure gives the required product ((M+1)+272) as a light brown coloured powder that is used as such in the next step.

Workup

  1. temperatureupon cooling
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying of the organic phase over magnesium sulphate, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-66539ccea3fa4a84a06590e9ccd7c632
Source dataset
uspto-grants-2013_05
Patent number
US08440595B2

Reaction notes

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