Nitrogen → HCID 22596141, compound

HRID 2301943Notes

Reaction equation

HRID 2301943 reaction equation
N#N.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13](=[N:18]O)[CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O.[Pd]>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]([NH2:18])[CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

7

Reactant 3

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 85521050HCID 85521050, compound

Product 1

HCID 22596141HCID 22596141, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To an N2 flushed solution of 3′,4′-dimethoxyvalerophenone oxime (0.5 grams, 2.1 mmol) in glacial acetic acid (10 milliliters) was added 0.1 grams of 5% Pd/C. The mixture was treated with 60 psi of H2 in a Parr Type Shaker for 24 hours. The catalyst was filtered off through celite and the filtrate was concentrated in vacuo to afford a yellow oil. The oil was taken up in water, the pH was adjusted to 12 using a saturated solution of sodium carbonate, and extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated to afford 0.41 grams (87%) of product as a yellow oil: 1H NMR (CDCl3) δ6.91-6.76(m, 3H), 3.98-3.78(m, 1H), 3.89(s, 3H), 3.87(s, 3H), 1.94-0.78(m, 11H).

Workup

  1. additionThe mixture was treated with 60 psi of H2 in a Parr Type Shaker for 24 hours
  2. filtrationThe catalyst was filtered off through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto afford a yellow oil
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-40cbbc497dd74e5797bfd8e32562ad4b
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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