Diethyl pyridine-3,5-dicarboxylate → HCID 69652400, compound

HRID 2212185Notes

Reaction equation

HRID 2212185 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=1)=[O:5])[CH3:2]>CCO.CC(O)=O.O=[Pt]=O>[C:4]([OH:5])(=[O:3])[CH3:6].[CH2:15]([O:14][C:12]([CH:10]1[CH2:11][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][NH:8][CH2:9]1)=[O:13])[CH3:16]

Participants

5

Reactant 1

HCID 78340Diethyl pyridine-3,5-dicarboxylate

Product 1

HCID 69652400HCID 69652400, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Hydrogenate pyridine-3,5-dicarboxylic acid diethyl ester (13.4 g, 60.0 mmol) in EtOH (100 mL) and HOAc (35 mL) with PtO2 (2.7 g, cat.) overnight at room temperature and 60 psi. Filter through celite and concentrated to dryness. Partition between sat. aq NaHCO3 and CHCl3. Extract 3× with CHCl3. Wash with sat. aq NaHCO3, wash with brine, dry over Na2SO4, filter and concentrate to dryness. MS(IS) 231.1 (M+2); Carried on without further purification.

Workup

  1. customat room temperature
  2. filtrationFilter through celite and
  3. concentrationconcentrated to dryness
  4. customPartition between sat. aq NaHCO3 and CHCl3
  5. extractionExtract 3× with CHCl3
  6. washWash with sat. aq NaHCO3
  7. washwash with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate to dryness
  11. customCarried on without further purification

Sources & evidence

ORD record
ord-120eeeba94b249e4be4f498bee33de73
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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