Sodium Hydroxide → 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile

HRID 2414749Notes

Reaction equation

HRID 2414749 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[C:24](#[N:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[NH2:27].[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[N:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:24]#[N:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 24813Phosphorus oxychlorideHCID 729132-AminobenzonitrileHCID 791761-Benzyl-3-pyrrolidone

Product 1

HCID 7584062-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrileYield 91.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized by mixing chloroform (25 mL), tetrahydrofuran (25 mL), 1-benzyl-2-pyrrolidinone (5.16 g, 29.4 mmol), phosphorus oxychloride (5.2 mL) and tin(IV) chloride (1.0 mL), stirring at room temperature for 1.5 hours, and adding anthranilonitrile (3.3 g, 27.9 mmol) in portions. The mixture was then stirred at 50° C. for 5 hours under heating and ice-water (15 mL) and 10% aqueous sodium hydroxide solution was added to make weak alkaline. The organic solvent was removed under reduced pressure and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and condensed under vacuum. The crude product was purified by flash chromatography (chloroform-methanol, 100:1) to yield 7.0 g (91%) Compound 24 as slightly yellow needles; mp 59-61° C.; IR (KBr): 2217, 1628, 1439, 1279 cm−1; 1H NMR (DMSO-d6): δ 7.06-7.69 (m, 9H), 4.83 (s, 2H), 3.46 (t, 2H), 2.60 (t, 2H), 2.10 (m, 2H); 13C NMR (CDCl3): δ 162.8, 156.3, 137.6, 133.7, 132.9, 128.7, 128.3, 127.4, 122.8, 121.7, 118.8, 105.9, 48.3, 47.3, 27.7, 19.6. Anal. Calcd. for C18H17N3(275.35): C, 78.52; H, 6.22; N, 15.26. Found: C, 78.37; H, 6.20; N, 15.17.

Workup

  1. customThe compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized
  2. stirringThe mixture was then stirred at 50° C. for 5 hours
  3. temperatureunder heating
  4. customThe organic solvent was removed under reduced pressure
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate and condensed under vacuum
  7. customThe crude product was purified by flash chromatography (chloroform-methanol, 100:1)

Sources & evidence

ORD record
ord-59607274f09643adba09e9c7346df39d
Source dataset
uspto-grants-2004_11
Patent number
US06815442B2

Reaction notes

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