Trifluoroacetate → HCID 67271522, compound

HRID 249709Notes

Reaction equation

HRID 249709 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)#[N:2].[F:12][C:13]([F:18])([F:17])[C:14]([O-:16])=[O:15].[H][H]>CO.[Ni]>[F:12][C:13]([F:18])([F:17])[C:14]([OH:16])=[O:15].[NH2:2][CH2:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 84468TrifluoroacetateHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 67271522HCID 67271522, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6-Cyanonicotinic acid as the trifluoroacetate (1 g) was dissolved in methanol (300 ml), treated with Raney nickel (0.224 g) and hydrogenated in a shaker autoclave at 80° C. for 20 h under 10 bar hydrogen pressure. Subsequently, the mixture was filtered, the residue was washed with a water/methanol mixture and the filtrate was concentrated. The residue was taken up with ACN/water and freeze-dried. 500 mg of product were obtained, which were sufficiently clean for use in the next stage.

Workup

  1. filtrationSubsequently, the mixture was filtered
  2. washthe residue was washed with a water/methanol mixture
  3. concentrationthe filtrate was concentrated
  4. customfreeze-dried

Sources & evidence

ORD record
ord-3c306bd708474fde9626f143e312348f
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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