2-Aminobiphenyl → HCID 178509175, compound
Reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[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=CC=1C1C=CC=CC=1.C(#N)CC#N.O.[NH2:39][NH2:40]>>[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[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:12]([NH2:13])=[N:40][N:39]=1Participants
Procedure
This compound 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) as described in Example 8, 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 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 85 mg (61%) of the title compound as an orange solid.
Workup
- customThis compound was prepared
- customPrecipitate formed in the reaction tube
- temperatureafter heating
- customthe reaction at 75° C. for 1 hr
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in ethyl acetate
- customprecipitated by the addition of hexanes
- customThe resulting solid was isolated by filtration
- customdried
Sources & evidence
- ORD record
- ord-a1d8b578c6e14adeae11975db4f8c8aa
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436915B1
Reaction notes
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