HCID 87180103, compound → ethyl 2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1406403Notes

Reaction equation

HRID 1406403 reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[C:7](=[C:13](/[NH2:15])\[CH3:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])C>CN(C)C=O>[CH2:11]([O:10][C:8]([C:7]1[CH:6]=[CH:5][C:4](=[O:3])[NH:15][C:13]=1[CH3:14])=[O:9])[CH3:12]

Participants

3

Reactant 1

HCID 87180103HCID 87180103, compound2×

Product 1

HCID 3299500ethyl 2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of intermediate (5a), (E)-4-[1-amino-eth-(Z)-ylidene]-pent-2-enedioic acid diethyl ester (51 g, 225 mmol) in N,N-dimethylformamide (250 mL) was heated at 175° C. for 24 hours to give a dark brown solution. The resulting solution was allowed to cool and a pale brown precipitate slowly formed. The precipitate was removed by filtration and the solids washed with dichloromethane (75 mL) and hexane (100 mL) to give a pale yellow powder. The solids were dried in vacuo (60° C.) to give the title compound as a pale yellow powder, 14.45 g (36%)

Workup

  1. customto give a dark brown solution
  2. temperatureto cool
  3. customa pale brown precipitate slowly formed
  4. customThe precipitate was removed by filtration
  5. washthe solids washed with dichloromethane (75 mL) and hexane (100 mL)
  6. customto give a pale yellow powder
  7. customThe solids were dried in vacuo (60° C.)

Sources & evidence

ORD record
ord-155454a047d541128ed8cdb61e4cad88
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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