Hydrochloric Acid → Dimethyl 5-methoxypyridine-2,4-dicarboxylate

HRID 1084331Notes

Reaction equation

HRID 1084331 reaction equation
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C[O-].[Na+].Cl.[C:20]([O-])(O)=[O:21].[Na+]>CO>[CH3:20][O:21][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 14256374HCID 14256374, compound

Product 1

HCID 18960802Dimethyl 5-methoxypyridine-2,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

300 mg of dimethyl 5-bromopyridine-2,4-dicarboxylate (from Example 3) are dissolved in 5 ml of absolute methanol, and 120 mg of sodium methylate are added. After 60 hours under reflux, the mixture is poured onto ice and 2 ml of 2N HCl, rendered alkaline with NaHCO3 and extracted with 2 portions of CH2Cl2. After the extract has been dried over MgSO4, the solvent is evaporated. 175 mg of a white solid remain.

Workup

  1. temperatureAfter 60 hours under reflux
  2. extractionextracted with 2 portions of CH2Cl2
  3. dry with materialAfter the extract has been dried over MgSO4
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-43f71b84e94447d69c235d0abaef1ff0
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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