4-(3,4-Dinitrophenoxy)-pyridine → 4-(3,4-Diamino-phenoxy)-pyridine

HRID 491580Notes

Reaction equation

HRID 491580 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)([O-])=O>CO.CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[NH2:17])[O:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 177560774-(3,4-Dinitrophenoxy)-pyridine

Product 1

HCID 177558374-(3,4-Diamino-phenoxy)-pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3,4-Dinitro-phenoxy)-pyridine (1.36 g, 5.21 mmol) was dissolved in 20 mL MeOH and 40 mL EtOAc. To the argon-degassed solution was added 10% by weight Pd/C (0.35 g). The reaction was vigorously stirred for 42 h at RT under 1 atm of H2 gas. The reaction was filtered through a Celite® plug. The solvent was removed under reduced pressure to obtain the title compound.

Workup

  1. customTo the argon-degassed solution
  2. additionwas added 10% by weight Pd/C (0.35 g)
  3. filtrationThe reaction was filtered through a Celite® plug
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-716356c01d714014a59af25ea60c68e3
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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