Ammonium formate → HCID 43609566, compound

HRID 1487131Notes

Reaction equation

HRID 1487131 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:8])([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89815860HCID 89815860, compound

Product 1

HCID 43609566HCID 43609566, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-Nitro-N-(tetrahydro-2H-pyran-4-yl)benzamide (360 mg, 1.439 mmol), ammonium formate (272 mg, 4.32 mmol) in methanol (20 ml) at 0° C., was added Pd/C (10%, 0.04 g) and the reaction mixture was stirred at 60° C. for 1 hrs. The reaction mixture was cooled to room temperature and filtered through celite, the filtrate was concentrated under vacuum. The residue was taken in ethyl acetate and the organic layer was washed with water and brine, dried over sodium sulfate and concentrated under vacuum to afford the title compound (300 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated under vacuum
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3af0b198d59b47bb9924d1df6e880942
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

Loading…