N-[4-(benzyloxy)phenyl]pyridine-2-carboxamide → HCID 11356337, compound

HRID 1807818Notes

Reaction equation

HRID 1807818 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 2425421N-[4-(benzyloxy)phenyl]pyridine-2-carboxamide

Product 1

HCID 11356337HCID 11356337, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of pyridine-2-carboxylic acid (4-benzyloxyphenyl)amide (7.7 g, 25.3 mmol) in 90% ethanol (110 mL) was hydrogenated (60 psi) over 10% palladium on carbon (0.8 g) at 50° C. for 4 hours. The catalyst was removed by filtration, and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel, using methanol/dichloromethane (DCM), 5/95, as the eluant, to give the product as a beige solid, 2.54 g (47%). MS m/z 215 (MH+). 1H NMR (DMSO-d6) δ 6.76 (d, 2H), 7.54 to 7.76 (m, 3H), 8.05 (t, 1H), 8.14 (d, 1H), 8.72 (d, 1H), 9.30 (s, 1H) and 10.41 (s, 1H). Anal. calcd for C12H10N2O2: C, 67.28; H, 4.71; N, 13.08. Found: C, 66.99; H, 4.56; N, 12.81.

Workup

  1. customat 50° C.
  2. customfor 4 hours
  3. customThe catalyst was removed by filtration
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b04c944aa8a84a77848b371b93a97652
Source dataset
uspto-grants-2013_01
Patent number
US08357715B2

Reaction notes

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