Benzaldehyde → 2-Benzylideneamino-4-methylbenzonitrile

HRID 651683Notes

Reaction equation

HRID 651683 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13].C(OCC)(=O)C>CCCCCCC>[CH:1](=[N:9][C:10]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8857Ethyl AcetateHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 217084982-Benzylideneamino-4-methylbenzonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Benzaldehyde(8.9 g, 84 mmol) is added to a suspension of 2-amino-4-methylbenzonitrile (10.0 g, 76 mmol) in heptane (250 mL), and the mixture refluxed under nitrogen overnight. The hot solution is decanted into a pre-warmed flask to leave the insoluble brown oil material behind, and the solution cooled to room temperature after adding ethyl acetate (2 mL). The resulting solid is filtered off and washed with heptane:ethyl acetate=100:1 (2×25 mL), and dried under high vacuum to give a beige powder (12.54 g, 57 mmol).

Workup

  1. temperaturethe mixture refluxed under nitrogen overnight
  2. customThe hot solution is decanted into a pre-warmed flask
  3. customto leave the insoluble brown oil material behind, and the solution
  4. filtrationThe resulting solid is filtered off
  5. washwashed with heptane
  6. dry with materialethyl acetate=100:1 (2×25 mL), and dried under high vacuum

Sources & evidence

ORD record
ord-62b48c9906dc4129be886a0cfd798713
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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