p-Toluidine → HCID 178424384, compound

HRID 2304430Notes

Reaction equation

HRID 2304430 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][N:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11].NC1C=CC(C)=CC=1.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:11][C:10]1[C:9](=[N:8][NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:14])[C:12]([NH2:13])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 7813p-ToluidineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)HCID 12450559CARBONYLCYANIDE2METHYLPHENYLHYDRAZONE

Product 1

HCID 178424384HCID 178424384, compoundYield 40%

Procedure

This compound was prepared using 92 mg (0.5 mmol) of 2-(o-tolylhydrazono)-malononitrile, which was derived from 4-toluidine (107 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Very little solid had formed after heating the reaction at 75° C. for 1 hr, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to room temperature and the solvent was evaporated. The residue was dissolved in ethyl acetate and then precipitated by the addition of hexanes. The resulting solid was isolated by filtration and dried to yield 43 mg (40%) of the title compound as a yellow solid.

Workup

  1. customThis compound was prepared
  2. customVery little solid had formed
  3. temperatureafter heating
  4. customthe reaction at 75° C. for 1 hr
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customprecipitated by the addition of hexanes
  8. customThe resulting solid was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-19019dc59fb1454aa352515c0968e36d
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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