Formamide → 2-Pyridinecarboxamide

HRID 2306138Notes

Reaction equation

HRID 2306138 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:8]([NH2:10])=[O:9]>CN(C)C1C=CN=CC=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Cl-].[Cl-].[Pd+2].C(#N)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:8]([NH2:10])=[O:9]

Participants

6

Reactant 2

HCID 713FormamideHCID 79772-Chloropyridine

Product 1

HCID 150702-Pyridinecarboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

0.255 g of bis(tricyclohexylphosphine)-palladium(II) dichloride, 5.458 g of 2-chloropyridine, 3.12 g of formamide, 4.64 g of 4-dimethylamino-pyridine and 25 ml of acetonitrile are placed in a 200 ml glass autoclave. The autoclave is closed, flushed with nitrogen three times and then 5 bars carbon monoxide are applied. The reaction mixture is heated to 120° C. and stirred for 18 hours. It is then cooled, and the suspension is mixed with ethyl acetate and water, and extracted. The aqueous phase is extracted by shaking 3 times with ethyl acetate, and afterwards the organic phases are collected, dried over magnesium sulphate and concentrated. The oil obtained is chromatographed over silica gel. The yield of title compound is 36% (part of the product remains in the water phase).

Workup

  1. customThe autoclave is closed
  2. customflushed with nitrogen three times
  3. temperatureIt is then cooled
  4. additionthe suspension is mixed with ethyl acetate and water
  5. extractionextracted
  6. extractionThe aqueous phase is extracted
  7. stirringby shaking 3 times with ethyl acetate
  8. customafterwards the organic phases are collected
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated
  11. customThe oil obtained
  12. customis chromatographed over silica gel

Sources & evidence

ORD record
ord-20d87d98f58e4c9f9302c29260e9adaf
Source dataset
uspto-grants-2002_08
Patent number
US06441233B1

Reaction notes

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