HCID 15672396, compound → HCID 15672397, compound

HRID 2255205Notes

Reaction equation

HRID 2255205 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1>Cl.O1CCCC1>[CH:3]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1)=[O:2]

Participants

4

Reactant 1

HCID 15672396HCID 15672396, compound

Product 1

HCID 15672397HCID 15672397, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of dimethyl 5-dimethoxymethylpyridine-2,3-dicarboxylate (6.57 g, 0.024 mol) in 2N HCl (15 mL) and tetrahydrofuran (25 mL) is stirred at reflux temperature for 2 hours. The tetrahydrofuran is removed in vacuo, the aqueous solution is diluted with water (to 30 mL) and extracted with methylene chloride. The combined methylene chloride extracts are dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound (4.51 g, 82%) as a yellow solid, mp 75°-77° C., identified by IR and NMR spectral analyses.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. customThe tetrahydrofuran is removed in vacuo
  3. additionthe aqueous solution is diluted with water (to 30 mL)
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined methylene chloride extracts are dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdd6cc29b5d440dea1977c009a964c70
Source dataset
uspto-grants-1993_08
Patent number
US05239070

Reaction notes

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