Aniline → N-Phenylisonicotinamide

HRID 31389

Reaction equation

HRID 31389 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 condensor 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-78af5c767acb4356bae4c3920e61f31c
Source dataset
uspto-grants-2008_09
Patent number
US07425639B2

Linked notes

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