Hydrochloric Acid → HCID 67509484, compound

HRID 623425Notes

Reaction equation

HRID 623425 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1.[ClH:15]>CO.[Pd]>[ClH:15].[F:14][C:2]([F:1])([F:13])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][NH2:12])[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59570383HCID 59570383, compound

Product 1

HCID 67509484HCID 67509484, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(2,2,2-trifluoroethoxy)picolinonitrile (0.71 g, 3.51 mmol, Step-1), hydrochloric acid (0.21 mL, 7.03 mmol) and palladium 10% on carbon (0.15 g) in methanol (35 mL) is vigorously stirred at room temperature under hydrogen atmosphere (0.3 MPa) for 4 hours. After filtration through a pad of celite, the filtrate is concentrated in vacuo. The residue is crystallized from ethyl acetate to give 0.43 g (44% yield) of the title compound as a white solid.

Workup

  1. filtrationAfter filtration through a pad of celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-1ddee77657fb49d983ecc31341447f67
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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