Aniline → N-Phenylisonicotinamide

HRID 2234263

Reaction equation

HRID 2234263 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>ClCCCl>[C:12]1([NH:11][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 220840N-Phenylisonicotinamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 4-necked RBF equipped with an overhead stirrer, J-Kem internal temperature probe, a reflux condenser and an addition funnel was placed isonicotinoyl chloride-hydrochloride (50 g, 0.28 mol). To this solid was added 500 ml of 1,2-dichloroethane and the slurry cooled to 0° C. using an ice/water bath. To the addition funnel was added a mixture of the aniline (31.4 g, 0.34 mol) and Et3N (59.5 g, 0.59 mol) in 50 ml of 1,2-dichloroethane. This mixture was slowly added to the slurry over 25 min. A slight exotherm was observed from 2.4° C. to 15° C. after the addition of the first 10 ml. The reaction mixture was observed to cool down slowly. The reaction mixture turned yellow and became heterogeneous. After 30 min., the ice bath was removed and the reaction heated to reflux for 1.5 h. Deionized water, 100 ml, was added and an off-white precipitate formed. The precipitate was collected by filtering through paper on a Buchner funnel and placed in a drying oven (60° C.) overnight to give 45 g (81% th) of an off-white crystalline solid.

Workup

  1. customInto a 4-necked RBF equipped with an overhead stirrer
  2. additionTo the addition funnel was added
  3. additionThis mixture was slowly added to the slurry over 25 min
  4. customwas observed from 2.4° C. to 15° C.
  5. additionafter the addition of the first 10 ml
  6. temperatureto cool down slowly
  7. customthe ice bath was removed
  8. temperaturethe reaction heated
  9. temperatureto reflux for 1.5 h
  10. additionDeionized water, 100 ml, was added
  11. customan off-white precipitate formed
  12. customThe precipitate was collected
  13. filtrationby filtering through paper on a Buchner funnel
  14. customplaced in a drying oven
  15. custom(60° C.) overnight to give 45 g (81% th) of an off-white crystalline solid

Sources & evidence

ORD record
ord-7c331de6990e44ad803b44bc370f3547
Source dataset
uspto-grants-2010_05
Patent number
US07709677B2

Linked notes

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