Ammonium formate → HCID 67332349, compound

HRID 1896743Notes

Reaction equation

HRID 1896743 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:23]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:22][C:19]([F:20])([F:21])[O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:23][C:8]=3[N:9]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67331521HCID 67331521, compound

Product 1

HCID 67332349HCID 67332349, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 5-nitro-2-(4-(trifluoromethoxy)phenyl)benzo[d]oxazole (850 mg, 2.62 mmol) in ethanol (20 mL) was added ammonium formate (827 mg, 13.1 mmol) and palladium on carbon (85 mg). The mixture was stirred at room temperature for 20 min, then filtrated through a pad of Celite®, and washed with ethyl acetate. The organic solution was washed with water, followed by brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 434 mg (56%) of the title compound (LCMS RT=6.51 min, MH+ 294.9)

Workup

  1. filtrationfiltrated through a pad of Celite®
  2. washwashed with ethyl acetate
  3. washThe organic solution was washed with water
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-80f91f73db04444a8f74cb62bb81918c
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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