Water → HCID 67153606, compound

HRID 1160873Notes

Reaction equation

HRID 1160873 reaction equation
[CH3:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.O>C(O)C.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 962WaterHCID 671534333-Methyl-5-nitro-2-[4-(trifluoromethyl)phenyl]pyridine

Product 1

HCID 67153606HCID 67153606, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 3-methyl-5-nitro-2-(4-trifluoromethyl-phenyl)-pyridine (3.5 g, 10.56 mmol) in ethanol (50 mL) is added palladium (10%) on carbon (0.700 g, 20% by wt.). The reaction is charged to 15 psi under a hydrogen atmosphere and allowed to stir for 4 hours. The reaction is diluted with ethyl acetate and Celite is added, followed by water. This mixture is then filtered through a pad of celite. The solution is concentrated, diluted with ethyl acetate, poured into a separatory funnel and the organic layer is washed with water and brine. The organic layer is dried over anhydrous sodium sulfate and concentrated. The product is used directly in the next step (2.74 g, 10.87 mmol).

Workup

  1. additionThe reaction is charged to 15 psi under a hydrogen atmosphere
  2. additionis added
  3. filtrationThis mixture is then filtered through a pad of celite
  4. concentrationThe solution is concentrated
  5. additiondiluted with ethyl acetate
  6. additionpoured into a separatory funnel
  7. washthe organic layer is washed with water and brine
  8. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-463df3b4734a4956af5871ce5995e721
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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