HCID 12545264, compound → N~1~-([1,1'-Biphenyl]-2-yl)benzene-1,2-diamine

HRID 383214Notes

Reaction equation

HRID 383214 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:14]=[CH:15][CH:16]=1)([O-])=O.[H][H]>[Pd].C(O)C>[C:12]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 12545264HCID 12545264, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13989156N~1~-([1,1'-Biphenyl]-2-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-nitrophenyl)biphenyl-2-amine (19.69 g, 67.8 mmol), 10% palladium on carbon (0.29 g, 0.27 mmol), and 150 mL of ethanol was added to a Parr hydrogenator bottle. The mixture was hydrogenated on a Parr hydrogenator until no more hydrogen was taken up by the solution. The solution was filtered through Celite to remove the catalyst, Celite was washed with dichloromethane, the filtrate was evaporated to yield a brown oil, 14.8 g (84%). The product was used for the next step without further purification.

Workup

  1. filtrationThe solution was filtered through Celite
  2. customto remove the catalyst, Celite
  3. washwas washed with dichloromethane
  4. customthe filtrate was evaporated
  5. customto yield a brown oil, 14.8 g (84%)
  6. customThe product was used for the next step without further purification

Sources & evidence

ORD record
ord-8fa2ac664396495a8847c2a25ca89096
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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