1,1'-Biphenyl, 2,2',6,6'-tetranitro- → HCID 12750378, compound

HRID 1026775Notes

Reaction equation

HRID 1026775 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:14]=1[N+:22]([O-])=O)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[C:13]1[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:22]

Participants

4

Reactant 1

HCID 1649461,1'-Biphenyl, 2,2',6,6'-tetranitro-

Product 1

HCID 12750378HCID 12750378, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under the protection of nitrogen gas, the 2,2′,6,6′-tetranitrobiphenyl (1.00 g, 3 mmol) and 100 mg 10% Pd/C were added into a 100 mL hydrogenation flask. Subsequently, 20 mL of methanol is added, and the resultant mixture was bubbled with nitrogen gas. The hydrogenation flask was placed in an autoclave, and was added 10 atm of hydrogen gas. After 6 hours, the reaction is completed. The resultant was filtered to remove Pd/C, and was rotary evaporated to remove the methanol. The residue was extracted with ethyl acetate and water, dried over anhydrous sodium sulfate, filtered, and votary evaporated, to afford the product in a yield of 88%.

Workup

  1. customthe resultant mixture was bubbled with nitrogen gas
  2. additionwas added 10 atm of hydrogen gas
  3. filtrationThe resultant was filtered
  4. customto remove Pd/C
  5. customwas rotary evaporated
  6. customto remove the methanol
  7. extractionThe residue was extracted with ethyl acetate and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customvotary evaporated, to afford the product in a yield of 88%

Sources & evidence

ORD record
ord-3252cdc1df9a4150a4782bc52a2aa36e
Source dataset
uspto-grants-2014_05
Patent number
US08729303B2

Reaction notes

Loading…