Triethylamine → 2-Chloro-N-(1H-pyrazol-5-yl)-3-pyridinecarboxamide

HRID 616006Notes

Reaction equation

HRID 616006 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:18][C:19]1[NH:23][N:22]=[CH:21][CH:20]=1>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]([NH:18][C:19]2[NH:23][N:22]=[CH:21][CH:20]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74561Pyrazol-3-ylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 203708142-Chloro-N-(1H-pyrazol-5-yl)-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

175 g. of 2-chloro-3-pyridinecarboxylic acid chloride are dissolved in 750 ml. of anhydrous dioxane containing 110 g. of triethylamine. At 10°, 83 g. of 5-aminopyrazole dissolved in 100 ml. of dioxane are added dropwise with stirring. After the addition is completed, the mixture is stirred overnight at room temperature, filtered and the precipitate washed with dioxane. The solvent is removed in vacuo and the oily residue crystallized with ethyl acetate. The product, 2-chloro-N-(1H-pyrazol-5-yl)-3-pyridinecarboxamide, is recrystallized from ethyl acetate, yield: 103 g. (46%); m.p. 162.8°.

Workup

  1. customAt 10°
  2. additionAfter the addition
  3. stirringthe mixture is stirred overnight at room temperature
  4. filtrationfiltered
  5. washthe precipitate washed with dioxane
  6. customThe solvent is removed in vacuo
  7. customthe oily residue crystallized with ethyl acetate
  8. customThe product, 2-chloro-N-(1H-pyrazol-5-yl)-3-pyridinecarboxamide, is recrystallized from ethyl acetate, yield: 103 g

Sources & evidence

ORD record
ord-c9f8905ed397470999528a79ab963505
Source dataset
uspto-grants-1978_02
Patent number
US04072680

Reaction notes

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