Ammonia → 3-Iodoquinolin-6-ol

HRID 2421525Notes

Reaction equation

HRID 2421525 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+].CN(C)CCN(C)C.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

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 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) (1.0 g), sodium iodide (1.34 g) and copper iodide (0.09 g) in dioxane (6.5 ml) was added N,N,N′,N′-tetramethyl-ethane-1,2-diamine (0.1 ml) in a sealed tube. The mixture was stirred at 120° C. for 12 h and upon cooling was treated with aqueous ammonia followed by aqueous hydrochloric acid. Extraction with ethyl acetate, drying of the organic phase over magnesium sulphate, filtration and evaporation under reduced pressure gave the required product (MH+ 272) as a light brown coloured powder that was 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-80c853557212485e89e745fbfae8454a
Source dataset
uspto-grants-2011_06
Patent number
US07956188B2

Reaction notes

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