Hydrochloric Acid → HCID 67056947, compound

HRID 1921277Notes

Reaction equation

HRID 1921277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9]/[CH:10]=[C:11](\[C:18]([O:20][CH3:21])=[O:19])/[CH:12]=[CH:13]/[C:14](OC)=[O:15].C[O-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86639846HCID 86639846, compound

Product 1

HCID 67056947HCID 67056947, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of dimethyl (2E,4Z)-4-{[(2,6-dichlorophenyl)amino]methylene}-2-pentenedioate (7.3 g) in MeOH (73 mL) was added 28% sodium methoxide in MeOH (4.3 mL). The mixture was refluxed for 8 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into 1 M HCl (140 ml) at 0° C. The resulting mixture was extracted with EtOAc (70 mL×2). The combined extracts were washed with saturated aqueous NaHCO3 (100 mL) and brine, dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was triturated with a mixture of EtOAc and hexane (1:3) to provide methyl 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (4.3 g).

Workup

  1. temperatureThe mixture was refluxed for 8 hr under a nitrogen atmosphere
  2. extractionThe resulting mixture was extracted with EtOAc (70 mL×2)
  3. washThe combined extracts were washed with saturated aqueous NaHCO3 (100 mL) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was triturated with a mixture of EtOAc and hexane (1:3)

Sources & evidence

ORD record
ord-d67e6a84c1cc41f28239a59398f04091
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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