N,N'-Dimethylethylenediamine → HCID 68725213, compound

HRID 408655Notes

Reaction equation

HRID 408655 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>CN(C)C=O.[OH-].[Na+].[Cu]I>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 43668381HCID 43668381, compound

Product 1

HCID 68725213HCID 68725213, compoundYield 38.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Chloro-6-iodo-2-methylquinoline (0.61 g; see step (ii) above), 2-pyrrolidinone (0.24 g), copper (I) iodide (0.038 g), potassium phosphate (0.5 g) and N,N′-dimethylethylenediamine (0.035 g) in dimethylformamide (3 mL) were heated in a microwave at 100° C. for 1 hour. The reaction mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and methanol. The desired fractions were concentrated and the sample evaporated to dryness. Trituration from ether gave the title compound as a white powder (0.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and methanol
  7. concentrationThe desired fractions were concentrated
  8. customthe sample evaporated to dryness

Sources & evidence

ORD record
ord-b5e93f6e838449da909eb75e95413def
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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