2-Aminobenzonitrile → 2-[N-(5-methyl-2-nitrobenzylidene)amino]benzonitrile

HRID 274132Notes

Reaction equation

HRID 274132 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=O>C1(C)C=CC=CC=1>[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=[N:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 729132-AminobenzonitrileHCID 118051105-Methyl-2-nitrobenzaldehyde

Product 1

HCID 200945252-[N-(5-methyl-2-nitrobenzylidene)amino]benzonitrileYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (167 ml) and 2-aminobenzonitrile (19.7 g, 167 mmol) were added to 5-methyl-2-nitrobenzaldehyde (27.5 g, 167 mmol) as obtained in Reference Example 1, and the mixture was stirred and refluxed for 14 hours, followed by cooling. The resultant crystals were filtered off, washed with a mixed solvent of hexane/toluene (2:1, 150 ml) and hexane (150 ml) twice to give 27.5 g of 2-[N-(5-methyl-2-nitrobenzylidene)amino]benzonitrile. In addition, the solid precipitated from the filtrate was filtered off and washed with hexane (100 ml and 50 ml) to give 10.0 g of the compound.

Workup

  1. customas obtained in Reference Example 1
  2. temperaturerefluxed for 14 hours
  3. temperatureby cooling
  4. filtrationThe resultant crystals were filtered off
  5. washwashed with a mixed solvent of hexane/toluene (2:1, 150 ml) and hexane (150 ml) twice

Sources & evidence

ORD record
ord-9274c858a04045b6946923ef4ef2faa2
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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