Picolinic acid → N-Phenylpicolinamide

HRID 1493135Notes

Reaction equation

HRID 1493135 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.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>CN(C)C=O.O>[C:23]1([NH:22][C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 6115AnilineHCID 14798Sodium HydroxideHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 7020657N-PhenylpicolinamideYield 32.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of carbonyldiimidazole (8.10 g) in dry dimethylformamide (100 mL) under N2 atmosphere, was added the picolinic acid (15.0 g) portionwise, then stirred for 30 minutes. Aniline (10.93 mL) was added rapidly dropwise, then stirred for 18 hours at room temperature. The reaction mixture was poured into water (400 mL), basified with 2.5N NaOH (25 mL) and stirred for 30 minutes while solid precipitated. The solid was collected by vacuum filtration, washed with water, and dried in vacuo. This tan solid was recrystallized from ether/hexane (1/1) to afford 7.69 g (32.3%) of an off-white solid, m.p. 75°-77° C.

Workup

  1. stirringstirred for 18 hours at room temperature
  2. stirringstirred for 30 minutes while solid
  3. customprecipitated
  4. filtrationThe solid was collected by vacuum filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customThis tan solid was recrystallized from ether/hexane (1/1)

Sources & evidence

ORD record
ord-e4174ec54018408380b0c8f4b7cb1174
Source dataset
uspto-grants-1991_06
Patent number
US05021418

Reaction notes

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