Hydrochloric Acid → HCID 22464475, compound

HRID 1935434Notes

Reaction equation

HRID 1935434 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[ClH:15]>C(O)C.[Pd]>[ClH:15].[ClH:15].[NH2:2][CH2:1][C:3]1[C:8]([O:9][CH2:10][C:11]([F:14])([F:12])[F:13])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22464526HCID 22464526, compound

Product 1

HCID 22464475HCID 22464475, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.53 g (2.62 mmol) of 2-cyano-3-(2,2,2-trifluoroethoxy)pyridine and 0.66 mL (7.87 mmol) of conc. HCl in 50 mL of ethanol was hydrogenated over 0.27 g of 10% palladium on carbon at 45 psi for 1.5 h. The catalyst was removed by filtration through a pad of Celite with EtOH. The solvents were removed at reduced pressure to give the title compound: 1H NMR (CD3OD) δ8.36 (d, 1H, 5.0 Hz), 7.73 (d,1H, 8.6 Hz), 7.54 (dd, 1H, 8.4, 5.0 Hz), 4.80 (q, 2H, 8.3 Hz), 4.33 (s, 2H).

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite with EtOH
  2. customThe solvents were removed at reduced pressure

Sources & evidence

ORD record
ord-58da966e0ffd455db1baa506df45a693
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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