Picolinic acid → HCID 2576380, compound

HRID 1709744Notes

Reaction equation

HRID 1709744 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]=[C:28]([F:30])[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]=[C:28]([F:30])[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 97092,4-DifluoroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 2576380HCID 2576380, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Picolinic acid (10.0 g, 81 mmol) was added to a solution of 1,1'-carbonyldiimidazole (13,13 g, 81 mmol) in dimethylformamide (80 mL) and the reaction mixture was stirred for 1 hour before introduction of 2,4-difluoroaniline (9.06 mL, 89 mmol). After 24 hours, the reaction mixture was poured into saturated sodium bicarbonate solution, extracted into ether, dried, concentrated, and recrystallized using a mixture of ether and petroleum ether to yield N-(2,4-difluorophenyl)-2-pyridine-carboxamide as a white solid (14.37 g, 76.0%) m.p. 90.5°-95° C.

Workup

  1. extractionextracted into ether
  2. customdried
  3. concentrationconcentrated
  4. customrecrystallized
  5. additiona mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-d4da6dd4481f463ba9db74bfc81aa84d
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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