2-Dimethylaminopyridine → 5-bromo-N,N-dimethylpyridin-2-amine

HRID 1790469Notes

Reaction equation

HRID 1790469 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[Br-:10].C([NH+](CCCC)CCCC)CCC>C(Cl)(Cl)Cl>[Br:10][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:9])[CH3:1])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 218852-DimethylaminopyridineHCID 13798051Tributylammonium bromide

Product 1

HCID 38030415-bromo-N,N-dimethylpyridin-2-amineYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Dimethylaminopyridine (1.0 ml) was dissolved in chloroform (60 ml). After adding tributylammonium bromide (3.88 g) thereto, the resultant mixture was stirred for 7 min. Then the reaction solution was washed with an aqueous solution of sodium thiosulfate and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate-methanol system) to give the title compound (1.097 g) as yellow crystals (yield: 72.0%).

Workup

  1. washThen the reaction solution was washed with an aqueous solution of sodium thiosulfate and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-8ab6efd27df644d79ffb16a0c7f0a1ec
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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