Acetic Acid → HCID 86625195, compound

HRID 419532Notes

Reaction equation

HRID 419532 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:8][C:7]=1[O:19][CH3:20])=[O:4].[CH3:23][C:24]([OH:26])=[O:25]>[Pt]=O>[C:24]([OH:26])(=[O:25])[CH3:23].[F:22][C:2]([F:1])([F:21])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:8][C:7]=1[O:19][CH3:20])=[O:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 59452593HCID 59452593, compound

Product 1

HCID 86625195HCID 86625195, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

2,2,2-Trifluoro-N-[5-methyl-2-(methyloxy)-4-(4-pyridinyl)phenyl]acetamide (2.37 g, 7.64 mmol) was placed in a 250 mL high pressure vessel and dissolved in 70 mL of HOAc. Platinum oxide (0.173 g, 0.76 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (60 psi). The solution stirred for 24 h. The vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to give the title compound (2.83 g, 7.46 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.11 (s, 1H), 6.86 (s, 1H), 3.76 (s, 3H), 3.14 (d, J=12.27 Hz, 2H), 2.82-2.91 (m, 1H), 2.72-2.81 (m, 2H), 2.20 (s, 3H), 1.81 (s, 3H), 1.64-1.75 (m, 4H).

Workup

  1. customThe flask was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove any H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

Sources & evidence

ORD record
ord-aae93e8af053429f848f424e6f91d9fc
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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