Acetic Acid → 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-4,6-dimethylpyridine

HRID 1740955Notes

Reaction equation

HRID 1740955 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH2:10]([CH2:14][C:15](=O)[CH3:16])[C:11]([CH3:13])=O.C(O)(=O)C>C1(C)C=CC=CC=1.O.O.O.C([O-])(=O)C.[Na+]>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([N:1]2[C:15]([CH3:16])=[CH:14][CH:10]=[C:11]2[CH3:13])[CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 215072-Amino-4,6-dimethylpyridine

Product 1

HCID 224907362-(2,5-Dimethyl-1H-pyrrol-1-yl)-4,6-dimethylpyridineYield 89%

Reagents, catalysts & solvents 2

HCID 23665404Sodium Acetate TrihydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-4,6-dimethylpyridine (20.0 g, 164 mmol), acetonylacetone (30 mL, 170 mmol), acetic acid (2.0 mL, 35 mmol), and sodium acetate trihydrate (200 mg, 1.5 mmol) in 140 mL of toluene was heated to reflux for 48 h in a flask connected to a Dean-Stark trap. After cooling to room temperature, the reaction mixture was washed with 50 mL each of 2.5 N aqueous sodium hydroxide, water, and saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated. The residue was distilled through a 1×10 cm Vigreaux column to give 29.09 g (89% yield) of 4,6-dimethyl-2-(2,5-dimethylpyrrol-1-yl)pyridine as an almost colorless liquid boiling at 93-97° C. (0.05 mm).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h in a flask
  3. washthe reaction mixture was washed with 50 mL each of 2.5 N aqueous sodium hydroxide, water, and saturated aqueous sodium chloride
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. customdecanted
  6. customevaporated
  7. distillationThe residue was distilled through a 1×10 cm Vigreaux column

Sources & evidence

ORD record
ord-ac9ad4db26484c37a11c64fde7f18e17
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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