Ammonia → HCID 67361367, compound

HRID 2091467Notes

Reaction equation

HRID 2091467 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][C:6]=2[Cl:13].[I-:14].[Na+].N>O1CCOCC1.[Cu](I)I>[Cl:13][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([I:14])=[CH:11]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5238Sodium IodideHCID 66717842HCID 66717842, compound

Product 1

HCID 67361367HCID 67361367, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 3-bromo-8-chloro-6-hydroxyquinoline (5.0 g) (preparation described in WO 2004/108663), sodium iodide (5.8 g) and copper iodide (0.37 g) in dioxane (65 ml) is added N,N″-dimethyl-ethane-1,2-diamine (0.34 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 (to 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)+306) 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-7af200d2b98a444eacbdbc0a0b5088ff
Source dataset
uspto-grants-2013_05
Patent number
US08440595B2

Reaction notes

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