Hydrochloric Acid → HCID 19010296, compound

HRID 1741600Notes

Reaction equation

HRID 1741600 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:15]([O:17]CC)=[O:16])[C:7]([C:10]([O:12]CC)=[O:11])=[N:8][CH:9]=1)[CH:2]=[CH2:3].[OH-].[Na+].Cl>CO.O>[CH2:1]([C:4]1[CH:5]=[C:6]([C:15]([OH:17])=[O:16])[C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14097637HCID 14097637, compound

Product 1

HCID 19010296HCID 19010296, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 6.07 g of diethyl 5-allylpyridine-2,3-dicarboxylate in 20 mL of methanol, stirred under nitrogen, is added slowly a solution of 3.3 g of sodium hydroxide in 13 mL water. After diluting the reaction mixture with 10 mL each of water and methanol, it is heated at reflux for 13/4 hours. The reaction is cooled in an ice bath, acidified to pH 3 with concentrated hydrochloric acid, and concentrated in vacuo to a damp solid. This solid is reevaporated from pyridine to afford the product as a brown solid, mp>250°(dec).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 13/4 hours
  3. temperatureThe reaction is cooled in an ice bath
  4. concentrationconcentrated in vacuo to a damp solid
  5. customThis solid is reevaporated from pyridine

Sources & evidence

ORD record
ord-3aee82f79c954523814aa81ae7f0ced6
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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