2,2'-Dinitrobiphenyl → 2,2'-Biphenyldiamine

HRID 2354000Notes

Reaction equation

HRID 2354000 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][C:11]=1[N+:16]([O-])=O)([O-])=O>[Pd].CCOC(C)=O>[NH2:1][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][C:11]=1[NH2:16]

Participants

4

Reactant 1

HCID 755292,2'-Dinitrobiphenyl

Product 1

HCID 150752,2'-BiphenyldiamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 9H was synthesized by an adaptation of a literature procedure, Gillespie et al. (2002) J. Org. Chem. 67:3450-3458. 2,2′-Dinitrobiphenyl (102.0 g, 417.5 mmol) and 10% Pd/C (16.4 g) were combined with 300 mL EtOAc in a hydrogenation vessel. The vessel was pressurized to 40 psi H2 for 3.5 h (when H2 was no longer being consumed). The slurry was filtered through a plug of celite. Rotary evaporation followed by drying on a vacuum line gave pure product as light yellow/orange powder in 100% yield. 1H NMR (CDCl3, 297K, 300 MHz): δ 3.71 (s, 4H), δ 6.79 (dd, 2H, J=8.0, 1.2 Hz), δ 6.84 (td, 2H, J=7.4, 1.2 Hz), δ 7.12 (dd, 2H, J=8.0, 1.5 Hz), δ 7.19 (td, 2H, J=7.4, 1.5 Hz). 13C NMR (CDCl3, 297K, 300 MHz): δ 115.58, δ 118.71, δ 124.62, δ 128.81, δ 131.08, δ 144.22. HRMS (ESI-EMM): m/z=185.1073 ([M+H]+), Δ=2.7 ppm.

Workup

  1. custom(when H2 was no longer being consumed)
  2. filtrationThe slurry was filtered through a plug of celite
  3. customRotary evaporation
  4. customby drying on a vacuum line
  5. customgave pure product as light yellow/orange powder in 100% yield

Sources & evidence

ORD record
ord-3355006572df400caad4d3f0fb9d924b
Source dataset
uspto-grants-2010_07
Patent number
US07750149B2

Reaction notes

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