2-Nitrobiphenyl → 2-Aminobiphenyl

HRID 718735Notes

Reaction equation

HRID 718735 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-])=O>[Pd].CO>[C:5]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 68292-Nitrobiphenyl

Product 1

HCID 70152-Aminobiphenyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Activated palladium on carbon (10% w/w, 0.25 g) was added to a solution of the nitro 2 (1.70 g, 8.53 mmol) in anhydrous methanol (100 mL). The reaction flask was purged thrice with H2 (g), pressurized to 5 bar with H2 (g), and mechanically shaken in a Parr hydrogenator for 12 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to yield the amine 3 as a yellow oil (1.44 g, quant.) that was used immediately in the next step.

Workup

  1. customThe reaction flask was purged thrice with H2 (g)
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-26dd9f85fde644a1a1352eb47eff316b
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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