2,5-Hexanedione → 5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

HRID 2306017Notes

Reaction equation

HRID 2306017 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][C:10](=O)[CH2:11][CH2:12][C:13](=O)[CH3:14]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:9])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 120436225-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-amino-5-bromopyridine (89.87 g, 0.5194 mol) in toluene (500 mL) was added 2,5-hexanedione (85.0 mL, 0.724 mol). The reaction flask was equipped with a Dean-Stark apparatus and the solution heated to reflux for 14 h. The cooled reaction solution was extracted with H2O (2×200 mL). The organic layer was added directly to a plug of SiO23″l×2″w and eluted with toluene (250 mL). This treatment removes a significant amount of color from the crude product. The resulting eluent was concentrated to a light amber oil, which solidified upon cooling to provide 128.76 g (99%) of the title compound.

Workup

  1. customThe reaction flask was equipped with a Dean-Stark apparatus
  2. temperaturethe solution heated
  3. temperatureto reflux for 14 h
  4. customThe cooled reaction solution
  5. extractionwas extracted with H2O (2×200 mL)
  6. additionThe organic layer was added directly to a plug of SiO23″l×2″w
  7. washeluted with toluene (250 mL)
  8. customThis treatment removes a significant amount of color from the crude product
  9. concentrationThe resulting eluent was concentrated to a light amber oil, which
  10. temperatureupon cooling

Sources & evidence

ORD record
ord-a4e42773440b422eb17e16068a427113
Source dataset
uspto-grants-2002_08
Patent number
US06441181B1

Reaction notes

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