Picolinic acid → HCID 2653165, compound

HRID 477033Notes

Reaction equation

HRID 477033 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([OH:21])=O.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.CCOCC>[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)=[O:21])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 97314-FluoroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 2653165HCID 2653165, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

An anhydrous solution of 1,1'-carbonyldiimidazole (13.13 g, 81 mmol) in dimethylformamide (80 mL) was treated with picolinic acid (10.0 g, 81 mmol), and after 1 hour 4-fluoroaniline (8.46 mL, 89 mmol) was introduced. After 27 hours the reaction mixture was poured into saturated sodium bicarbonate solution (900 mL) and ether (400 mL). The aqueous layer was extracted again with ether (3×400 mL) and the ethereal layers were dried and concentrated. The crude solid residue was recrystallized from a mixture of ether and petroleum ether to yield N-(4-fluorophenyl)-2-pyridinecarboxamide (11.6 g, 66%) as beige crystals, m.p. 100°-103° C.

Workup

  1. extractionThe aqueous layer was extracted again with ether (3×400 mL)
  2. customthe ethereal layers were dried
  3. concentrationconcentrated
  4. customThe crude solid residue was recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-65054597e4c241ee961b41c8af3d6d42
Source dataset
uspto-grants-1989_12
Patent number
US04886821

Reaction notes

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