Hydrochloric Acid → HCID 21847049, compound

HRID 1741632Notes

Reaction equation

HRID 1741632 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[N:18](C)[C:19](=O)C.Cl>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[NH:18][CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 23206014HCID 23206014, compound

Product 1

HCID 21847049HCID 21847049, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 90.6 g of 6-methyl-5-(N-methylacetamido)-pyridine-2,3-dicarboxylic acid, diethyl ester in 700 mL absolute ethanol is treated with 60 mL of concentrated hydrochloric acid, and the solution is heated at reflux for 17 hours. The reaction is cooled, 75 mL of concentrated hydrochloric acid is added, and the reaction is heated at reflux for another 8 hours. The solution is concentrated in vacuo; the residue is stirred in water and basified to pH 8 using a saturated bicarbonate solution. The mixture is then extracted with methylene chloride, and the extracts are dried and concentrated in vacuo to afford the desired product as an oil.

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux for 17 hours
  3. temperatureThe reaction is cooled
  4. temperaturethe reaction is heated
  5. temperatureat reflux for another 8 hours
  6. concentrationThe solution is concentrated in vacuo
  7. extractionThe mixture is then extracted with methylene chloride
  8. customthe extracts are dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a3ba55e05004e7cb4b8c7706e6bb40b
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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