2-Cyano-4'-methylbiphenyl → HCID 6860513, compound

HRID 1439877Notes

Reaction equation

HRID 1439877 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Na].[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)#[N:9]>CS(C)=O.O.C(OCC)(=O)C.CO>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([C:11]2[C:10]([C:8](=[N:2][OH:3])[NH2:9])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 1455122-Cyano-4'-methylbiphenylHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 6860513HCID 6860513, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of hydroxylamine hydrochloride (17.9 g) in dimethyl sulfoxide (120 ml) was added a methanol solution of sodium methoxide prepared from metallic sodium (5.92 g) and anhydrous methanol (50 ml). The mixture was stirred for 10 minutes at room temperature, to which was added 2'-cyano-4-methylbiphenyl (10 g). The reaction mixture was stirred for 5 hours at 100° C. After cooling, the reaction mixture was distributed into ethyl acetate and water, and the aqueous layer was subjected to extraction with ethyl acetate. The organic layers were combined, washed with water and dried, then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as white amorphous product (11.2 g, 96%).

Workup

  1. stirringThe reaction mixture was stirred for 5 hours at 100° C
  2. temperatureAfter cooling
  3. extractionthe aqueous layer was subjected to extraction with ethyl acetate
  4. washwashed with water
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3ee7f10f85524c9fb1d00d73c5ed414b
Source dataset
uspto-grants-1996_03
Patent number
US05496835

Reaction notes

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