2,6-Bis(trifluoromethyl)-3-methoxycarbonyl-4-chloropyridine → Methyl 2,6-bis(trifluoromethyl)nicotinate

HRID 1253123Notes

Reaction equation

HRID 1253123 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7](Cl)[CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[N:4]=1>CO.[Pd]>[F:18][C:2]([F:1])([F:19])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[N:4]=1

Participants

4

Reactant 1

HCID 138828782,6-Bis(trifluoromethyl)-3-methoxycarbonyl-4-chloropyridine

Product 1

HCID 11507333Methyl 2,6-bis(trifluoromethyl)nicotinateYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

20 g (0.065 mole) of the product of Example 6 in 100 ml of methanol was hydrogenated for 2 days at room temperature and at 50 p.s.i. in the presence of 2 g of 10% Pd/C. The catalyst was filtered off and the solvent from the filtrate was removed under vacuum. The residue was taken up in ethyl ether, washed with H2O, 2X with sat. NaHCO3, 2X with H2O and dried over MgSO4. The ether was removed under vacuum and the residue was purified by HPLC (15% Et. Acet./Hexane) to yield 11.3 g (64%) of a clear liquid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent from the filtrate was removed under vacuum
  3. washwashed with H2O, 2X with sat. NaHCO3, 2X with H2O
  4. dry with materialdried over MgSO4
  5. customThe ether was removed under vacuum
  6. customthe residue was purified by HPLC (15% Et. Acet./Hexane)

Sources & evidence

ORD record
ord-7bd3885c82594826aaa4b4cac3c8c511
Source dataset
uspto-grants-1988_05
Patent number
US04747871

Reaction notes

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