4-Nitro-1,1'-biphenyl → N-hydroxy-4-aminobiphenyl

HRID 75103

Reaction equation

HRID 75103 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=[O:2].O.NN>O1CCCC1.[Rh]>[C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([NH:1][OH:2])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 71144-Nitro-1,1'-biphenylHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 81261N-hydroxy-4-aminobiphenylYield 99.5%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-nitrobiphenyl (400 mg, 2.008 mmol) and 5% rhodium on carbon (15 mg, 0.146 mmol) in tetrahydrofuran (15 ml), hydrazine hydrate (0.200 ml, 2.61 mmol) was added, and gas evolution was observed. The reaction mixture was stirred at RT for 25 minutes, then it was partitioned between diethyl ether (90 ml) and brine (20 ml), and the phases were separated. The aqueous phase was extracted with diethyl ether (90 ml), and the combined organic extracts were dried (Na2SO4) and concentrated to give 370 mg of the desired compound (89% purity) and about. The mixture was used as such for the next step.

Workup

  1. additionwas added
  2. customit was partitioned between diethyl ether (90 ml) and brine (20 ml)
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with diethyl ether (90 ml)
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5c3d895f9754649bd01c33d012c155b
Source dataset
uspto-grants-2014_09
Patent number
US08835412B2

Linked notes

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