Dimethyl 3,4-pyridinedicarboxylate → HCID 74371465, compound

HRID 712499Notes

Reaction equation

HRID 712499 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[C:3]([C:11]([O:13][CH3:14])=[O:12])[CH:2]=1>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:2]1

Participants

4

Reactant 1

HCID 596231Dimethyl 3,4-pyridinedicarboxylate

Product 1

HCID 74371465HCID 74371465, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of dimethyl pyridine-3,4-dicarboxylate (1.00 g, 5.10 mmol, 1 eq) and Pd(OH)2 (20 mg, 0.2 eq) in 20 mL of acetic acid was heated at 80° C. overnight under H2, and then cooled to room temperature. The resulted mixture was filtered and concentrated in vacuo. To the mixture was added 100 mL of water. The pH was adjusted to 7-8 by adding NH3H2O. The mixture was extracted with CH2Cl2 (50 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as pale yellow oil (600 mg, 57.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 201.15 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulted mixture was filtered
  3. concentrationconcentrated in vacuo
  4. additionTo the mixture was added 100 mL of water
  5. additionby adding NH3H2O
  6. extractionThe mixture was extracted with CH2Cl2 (50 mL×3)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db1226b59a3448cdaf59049724b33d5b
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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