Pyridine → HCID 21462913, compound

HRID 840266Notes

Reaction equation

HRID 840266 reaction equation
[C:1](Cl)([Cl:3])=[O:2].[NH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[ClH:3].[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([N:5]=[C:1]=[O:2])[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 100093-Aminopyridine

Product 1

HCID 21462913HCID 21462913, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1.93 solution of phosgene in toluene (20%) (584 mL) was diluted with dry CH2Cl2 (1 L) and the mixture was stirred at 0° C. under nitrogen atmosphere. A solution of 3-aminopyridine (21.1 grams) and dry pyridine (19 mL) dissolved in dry CH2Cl2 (600 mL) was added dropwise to the stirred solution at 0° C. over a period of 5.5 hours. The mixture was stirred at 0-25° C. for an additional 48 hours. A stream of nitrogen was passed through the solution to remove most of the phosgene and the solution was then evaporated until almost all of the solvent was removed to give the title compound which was then taken up in dry pyridine (850 mL) to give a stock solution of the title compound.

Workup

  1. additionwas added dropwise to the stirred solution at 0° C. over a period of 5.5 hours
  2. stirringThe mixture was stirred at 0-25° C. for an additional 48 hours
  3. customto remove most of the phosgene
  4. customthe solution was then evaporated until almost all of the solvent
  5. customwas removed

Sources & evidence

ORD record
ord-25006a80444f4e46ace1ac53934e5c1d
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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