Picolinic acid → HCID 9413884, compound

HRID 1709749Notes

Reaction equation

HRID 1709749 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25].C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 95842-FluoroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 9413884HCID 9413884, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Picolinic acid (10.0 g, 81 mmol) was added to a solution of 1,1'-carbonyldiimidazole (13.18 g, 81 mmol) in anhydrous dimethylformamide (80 mL), followed by the addition of 2-fluoroaniline (8.6 mL, 89 mmol) 1 hour later. The reaction mixture was poured into saturated sodium bicarbonate solution (900 mL) after 26 hours, and extracted with ether (3×400 mL). The dried organic material was concentrated in vacuo and recrystallized from a mixture of ether and petroleum ether to yield N-(2-fluorophenyl)-2-pyridinecarboxamide as a white solid (11.81 g) m.p. 112°-115° C.

Workup

  1. extractionextracted with ether (3×400 mL)
  2. concentrationThe dried organic material was concentrated in vacuo
  3. customrecrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-f8d1d2f8787b4438bf054c1728155d9c
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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