Hydrazine hydrate (1:1) → HCID 178507433, compound

HRID 854078Notes

Reaction equation

HRID 854078 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.O.NN>CCO.O.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=3)[NH:10][C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178526539HCID 178526539, compound

Product 1

HCID 178507433HCID 178507433, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 6-Nitro-2-(4-nitrophenyl)-3H-imidazo [4,5-b]pyridine (4) (0.5 g, 1.75 mmol) in EtOH (40 mL) was added Raney Ni° (1 g, slurry in H2O) followed by hydrazine hydrate (2 mL) dropwise over 5 minutes. The reaction mixture was stirred at room temperature until the reaction subsided and was then heated at 100° C. for 1 h. The hot solution was filtered through celite and the filtrate concentrated under reduced pressure. Water was added to the residue resulting in the formation of an off white solid that was collected by filtration, rinsed with H2O and air dried. The solid was then dried in vacuuo at room temperature to give 5 as a light tan solid (0.318 g, 1.4 mmol, 81%) 1H NMR (500 MHz, DMSO-d6) δ12.27 (apparent d, 1H), 7.77 (br s, 2H), 7.70 (br s, 1H) 6.97 (br s, 1H), 6.63 (d, J=8.51 Hz, 2H), 5.57 (br s, 2H), 4.97 (br s, 2H)

Workup

  1. temperaturewas then heated at 100° C. for 1 h
  2. filtrationThe hot solution was filtered through celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionWater was added to the residue
  5. customresulting in the formation of an off white solid
  6. filtrationthat was collected by filtration
  7. washrinsed with H2O and air
  8. customdried
  9. customThe solid was then dried in vacuuo at room temperature

Sources & evidence

ORD record
ord-0aa8c69c3d684b059ef99c3db1a2a314
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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