4-Chloropyridine → HCID 10797035, compound

HRID 2248366Notes

Reaction equation

HRID 2248366 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[NH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1>COCCOCCOC.O.C(=O)([O-])[O-].[Na+].[Na+]>[N:9]1([NH:8][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10]1

Participants

6

Reactant 2

HCID 122884-ChloropyridineHCID 1365891-Aminopyrrole

Product 1

HCID 10797035HCID 10797035, compoundYield 57.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 4-chloropyridine (15 g) and N-aminopyrrole (18 g) in 225 ml of diglyme was stirred at 150° C. for one hour and thereafter cooled, diluted with water and basified with sodium carbonate. The mixture was extracted with ethyl acetate, and the organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. This oil was purified by high performance liquid chromatography (HPLC hereafter) using silica gel and ethyl acetate to give 12 g of a solid, mp 150° C. Five grams of the solid was recrystallized twice from benzene to give 2.8 g of crystals, mp 153°-154° C.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionthe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customThis oil was purified by high performance liquid chromatography (HPLC hereafter)

Sources & evidence

ORD record
ord-507cf55a59ba4439b62427a4b46d8437
Source dataset
uspto-grants-1991_08
Patent number
US05039687

Reaction notes

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