Hydrochloric Acid → Ethyl 5-ethyl-4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1508686Notes

Reaction equation

HRID 1508686 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]([NH:8]/[C:9](/[CH3:18])=[C:10](/[CH2:16][CH3:17])\[C:11]([O:13]CC)=O)=[O:7])[CH3:2].C[O-].[Na+].Cl>CCO>[CH2:16]([C:10]1[C:11]([OH:13])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:19])[C:6](=[O:7])[NH:8][C:9]=1[CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 90338651ethyl (Z)-3-[(3-ethoxy-3-oxo-propanoyl)amino]-2-ethyl-but-2-enoate

Product 1

HCID 54706937Ethyl 5-ethyl-4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50-mL round bottom flask was charged with ethyl (Z)-3-[(3-ethoxy-3-oxo-propanoyl)amino]-2-ethyl-but-2-enoate (540 mg, 2 mmol, 1 eq.), sodium methoxide (750 mg, 6.8 mmol, 3.4 eq. 25 wt. % in MeOH) and EtOH (10 ml). The mixture was stirred under reflux for 1 hr. After cooling to room temperature, the mixture was acidified by addition of 2N HCl aq. (5 ml) and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to afford crude ethyl 5-ethyl-4-hydroxy-6-methyl-2-oxo-1H-pyridine-3-carboxylate (205 mg, 46% yield) as yellow solid.

Workup

  1. temperatureunder reflux for 1 hr
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-3b0e422f674f4b0485f0b998a7c8143b
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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