Picolinic acid → HCID 14510254, compound

HRID 1709742Notes

Reaction equation

HRID 1709742 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:24]=[C:25]([CH:27]=[C:28]([F:30])[CH:29]=1)[NH2:26].C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:22][C:23]1[CH:24]=[C:25]([NH:26][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH:27]=[C:28]([F:30])[CH:29]=1

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 682631,1'-CarbonyldiimidazoleHCID 965953,5-DifluoroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 14510254HCID 14510254, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Picolinic acid (13.0 g, 106 mmol) was added to a solution of 1,1'-carbonyldiimidazole (17.11 g, 106 mmol) in dry dimethylformamide (100 mL) and the reaction stirred for 1 hour, before introduction of 3,5-difluoroaniline (15.0 g, 116 mmol). After 3 days, the reaction mixture was poured into saturated sodium bicarbonate solution (1 L) and extracted with ether (2×500 mL). The organic layers were dried and concentrated to give a solid, which was recrystallized from a mixture of ether and petroleum ether to give N-(3,5-difluorophenyl)-2-pyridinecarboxamide (17.15 g, 69%) m.p. 111°-113° C.

Workup

  1. extractionextracted with ether (2×500 mL)
  2. customThe organic layers were dried
  3. concentrationconcentrated
  4. customto give a solid, which
  5. customwas recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-9eaaa6133c4e4c6ca7abd9775e85a2df
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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