Dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate → 2,6-Dimethyl-4-phenyl pyridine-3,5-dicarboxylic acid dimethyl ester

HRID 1018506Notes

Reaction equation

HRID 1018506 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]([C:16]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:20]([C:28]([O:30][CH3:31])=[O:29])=[C:19]([CH3:32])[NH:18][C:17]=1[CH3:33])=[O:15]>C(Cl)Cl>[CH3:12][O:13][C:14]([C:16]1[C:17]([CH3:33])=[N:18][C:19]([CH3:32])=[C:20]([C:28]([O:30][CH3:31])=[O:29])[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:15]

Participants

4

Reactant 2

HCID 129839Dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 109575212,6-Dimethyl-4-phenyl pyridine-3,5-dicarboxylic acid dimethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Over a suspension of 119 g (0.1 mol) of pyridinium chlorochromate absorbed on alumina in 330 ml of CH2Cl2, 10 g (0.033 mol) of 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester were portionwise added with stirring. The mixture was maintained with stirring at room temperature for 8 hours. The remaining solid was eliminated by filtration, and the liquid was washed with water (3×500 ml), dried over anh. Na2SO4, and concentrated at reduced pressure, to dryness. The product was obtained as a solid, (mp 133-5° C., MeOH) with a yield of 75%.

Workup

  1. additionwere portionwise added
  2. temperatureThe mixture was maintained
  3. stirringwith stirring at room temperature for 8 hours
  4. filtrationThe remaining solid was eliminated by filtration
  5. washthe liquid was washed with water (3×500 ml)
  6. dry with materialdried over anh. Na2SO4
  7. concentrationconcentrated at reduced pressure, to dryness
  8. customThe product was obtained as a solid, (mp 133-5° C., MeOH) with a yield of 75%

Sources & evidence

ORD record
ord-24a97d4a312e4d6882cf6c6609fc304d
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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