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

HRID 742211Notes

Reaction equation

HRID 742211 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° 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-dihydro-6-oxo-2,3-pyridinedicarboxylate as a yellow solid in quantitative yield.

Workup

  1. customis saturated at 20° C
  2. concentrationis then concentrated in vacuo
  3. dissolutionThe resulting residue is dissolved in water
  4. extractionextracted into methylene chloride
  5. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d4978ae0cb74b71a9d91a619b091b76
Source dataset
uspto-grants-1996_09
Patent number
US05554579

Reaction notes

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