3-Nitro[1,1'-biphenyl]-2-amine → 102877-92-9

HRID 1401118Notes

Reaction equation

HRID 1401118 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Fe].CC(O)=O>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 131499333-Nitro[1,1'-biphenyl]-2-amine

Product 1

HCID 18968019102877-92-9

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-3-nitrobiphenyl d (0.613 g, 2.86 mmol) was purged under nitrogen for 30 minutes then HOAc (5 mL) was added followed by iron powder (0.4895 g, 8.76 mmol). The sample was heated at 60° C. for 30 minutes then HOAc (5 mL) was added. The sample was stirred at 60° C. for 1 hour then poured into ice. The sample was extracted with EtOAc (3×100 mL). The EtOAc extracts were washed with saturated NaHCO3 (3×100 mL. The EtOAc layer was dried over MgSO4, filtered, and concentrated to give 2,3-diaminobiphenyl e (0.439 g, 2.38 mmol, 83%).

Workup

  1. customwas purged under nitrogen for 30 minutes
  2. additionHOAc (5 mL) was added
  3. additionthen poured into ice
  4. extractionThe sample was extracted with EtOAc (3×100 mL)
  5. washThe EtOAc extracts were washed with saturated NaHCO3 (3×100 mL
  6. dry with materialThe EtOAc layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8eb068e5d8fc4e4081fa55a501164e4d
Source dataset
uspto-grants-2014_12
Patent number
US08907092B2

Reaction notes

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