Hydrochloric Acid → Diethyl 5-amino-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

HRID 1733841Notes

Reaction equation

HRID 1733841 reaction equation
Cl.C([NH:5][C:6]1[C:11](=[O:12])[NH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=1)(=O)C>C(O)C>[NH2:5][C:6]1[C:11](=[O:12])[NH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19958266Diethyl 5-acetamido-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Product 1

HCID 19958246Diethyl 5-amino-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen chloride gas is bubbled into a solution of diethyl 5-acetamido-1, 6-dihydro-6-oxo-2,3-pyridinedicarboxylate (5.2 g, 0.018 mol) dissolved in absolute ethanol (400 mL) until the solution is saturated at 20.degree . C. The reaction is stirred at room temperature overnight and is then concentrated in vacuo. The resulting residue is dissolved in water, neutralized with solid sodium bicarbonate, and extracted into methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give diethyl 5-amino-1,6-d ihydro-6-oxo-2,3-pyridinedicarboxylate as a yellow solid in quantitative yield.

Workup

  1. concentrationis then concentrated in vacuo
  2. dissolutionThe resulting residue is dissolved in water
  3. extractionextracted into methylene chloride
  4. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15fa21b4109342edbba83414983ea9d3
Source dataset
uspto-grants-1996_07
Patent number
US05532207

Reaction notes

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