Water → 5-Iodo-N,N-dimethylpyridin-2-amine

HRID 454809Notes

Reaction equation

HRID 454809 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][N:4]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC.O>CC(N(C)C)=O>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][N:4]=1)[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11253290(5-Iodo-pyridin-2-yl)-methyl-amine

Product 1

HCID 234385795-Iodo-N,N-dimethylpyridin-2-amineYield 57%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

The obtained 2-(N-monomethylamino)-5-iodopyridine (99, 1.00 g, 4.27 mmol), potassium carbonate (2.95 g, 21.36 mmol) and iodomethane (145 mg, 8.546 mmol) were dissolved in dimethylacetamide (30 mL), and the reaction mixture was heated at 90° C. for 24 hours, followed by adding water. Organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-(N,N-dimethylamino)-5-iodopyridine (100, 603 mg, 57%).

Workup

  1. extractionOrganic compounds were extracted with ethyl acetate
  2. customevaporated after a treatment with sodium sulfate
  3. customPurification

Sources & evidence

ORD record
ord-f7704ee6c4784f8ab3530aa48939cf40
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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