2-Aminobiphenyl → HCID 178509179, compound

HRID 2095120Notes

Reaction equation

HRID 2095120 reaction equation
C1(C2C=CC=CC=2)C=CC=CC=1[NH:7][N:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11].N[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(#N)CC#N.O.[NH2:39][NH2:40]>>[C:22]1([C:27]2[CH:32]=[C:31]([NH:7][N:8]=[C:9]3[C:10]([NH2:11])=[N:40][N:39]=[C:12]3[NH2:13])[CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:21]=1

Participants

5

Reactant 4

HCID 70152-AminobiphenylHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 21955033HCID 21955033, compound

Product 1

HCID 178509179HCID 178509179, compound

Procedure

4-(3-phenylphenylhydrazono)-4H-pyrazole-3,5-diamine was prepared using 123 mg (0.5 mmol) of 2-[(biphenyl-2-yl)hydrazono]malononitrile, which was derived from 2-aminobiphenyl (169 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube immediately after the addition of the hydrazine hydrate then the solution cleared. Very little solid remained 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 ambient 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 85 mg (61%) of the compound as an orange solid.

Workup

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

Sources & evidence

ORD record
ord-0c9a5639250342239ffdd4165aac7d2f
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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