HCID 23499398, compound → HCID 23518819, compound

HRID 1836351Notes

Reaction equation

HRID 1836351 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[C:7]([C:9]1[CH:14]=[CH:13][N:12]([CH3:15])[CH2:11][CH:10]=1)=[O:8]>CO.[Pt]=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[OH:8])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 23499398HCID 23499398, compound

Product 1

HCID 23518819HCID 23518819, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[3-methoxybenzoyl]-1-methylpyridine iodide (730 mg, 2.1 mmol) and platinum oxide (100 mg, 0.44 mmol) in methanol was stirred under a hydrogen atmosphere for 2 h. The catalyst was filtered and washed with methanol then water. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methylene chloride, washed with 1N sodium hydroxide, dried over sodium sulfate and concentrated in vacuo to give 490 mg of a clear colorless oil. Purification by radial chromatography (silica gel, 2000 micron rotor, methylene chloride:methanol:ammonium hydroxide, 100:10:1) gave 425 mg (87%) of a white solid. Mp 102-104° C. MS(m/e): 235(M+).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in methylene chloride
  5. washwashed with 1N sodium hydroxide
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f6045f0a9b4455f89104d752e9075ec
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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