HCID 18319180, compound → HCID 18319307, compound

HRID 1701000Notes

Reaction equation

HRID 1701000 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1)#[N:2]>CO.ClCCl.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[C:10]([CH3:18])[CH:11]=1

Participants

5

Reactant 1

HCID 18319180HCID 18319180, compound

Product 1

HCID 18319307HCID 18319307, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(4-Cyanophenyl)-2-methyl-4-nitrobenzene (9.7 gm, 40.76 mmol) was dissolved in a mixture of methanol and dichloromethane (1:1, 400 mL) and hydrogenated over 10% palladium on charcoal (970 mg) at 3 bar and 20° C. for 18 h. The mixture was filtered through Arbocel filter aid and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate 20:1 to 1:1) to give 4-amino-1-(4-cyanophenyl)-2-methylbenzene (2.5 gm, 30%) as a brown oil.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate 20:1 to 1:1)

Sources & evidence

ORD record
ord-08f7e4b6286441888f5e545efdfdb82a
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

Loading…