p-Toluidine → 4-(p-Tolylamino)butanenitrile

HRID 389998Notes

Reaction equation

HRID 389998 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][CH2:18][C:19]#[N:20]>C(#N)C>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([NH:1][CH2:16][CH2:17][CH2:18][C:19]#[N:20])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 11430Potassium CarbonateHCID 214124-Bromobutyronitrile

Product 1

HCID 213325214-(p-Tolylamino)butanenitrileYield 78.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

p-Toluidine (10.407 g, 97.116 mmol) was dissolved in anhydrous acetonitrile and, after adding potassium carbonate (49.9 g, 361.272 mmol), stirred at room temperature for 10 minutes. After slowly adding 4-bromobutyronitrile (10.1 mL, 101.972 mmol) to the resultant reaction mixture, reaction was carried out at 100° C. for 2 days. The mixture was cooled to room temperature and the produced solid was removed by filtering. The filtrate was concentrated under reduced pressure. A target compound (13.23 g, 78.2%) was yielded. A target compound was used in the next step without further purification.

Workup

  1. waitwas carried out at 100° C. for 2 days
  2. temperatureThe mixture was cooled to room temperature
  3. customthe produced solid was removed
  4. filtrationby filtering
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-85250aa7e0a14936889f6b9ba4cbf577
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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