Ammonium formate → HCID 58118725, compound

HRID 1630076Notes

Reaction equation

HRID 1630076 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:13]=[C:11]([NH2:12])[C:10]([NH2:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67010061HCID 67010061, compound

Product 1

HCID 58118725HCID 58118725, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(4-fluorophenoxy)-2-nitroaniline (410 mg, 1.65 mmol), ammonium formate (520 mg, 8.26 mmol), 10% palladium on carbon (123 mg, 0.116 mmol) and methanol (10 mL) was stirred at ambient temperature for 30 minutes. The mixture was filtered and filtrate was concentrated. Product was purified from the residue by silica gel column chromatography (eluted with a 2:3→1:2 of hexane/EtOAc) to give 4-(4-fluorophenoxy)benzene-1,2-diamine (370 mg, quant) as a brown oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationfiltrate was concentrated
  3. customProduct was purified from the residue by silica gel column chromatography (
  4. washeluted with a 2:3→1:2 of hexane/EtOAc)

Sources & evidence

ORD record
ord-b35ed5676ceb447285446c585580905f
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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