Acetic Acid → Ethyl 5-cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylate

HRID 1629804Notes

Reaction equation

HRID 1629804 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]([CH3:23])([CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:5])#[N:2].O.[OH-].[Li+].CC(O)=O>C1COCC1.O.CCOC(C)=O>[C:1]([C:3]1[C:4](=[O:5])[NH:6][C:7]([CH3:23])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)#[N:2]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86685897Ethyl 2-(2-cyanoacetamido)-2-methyl-4-oxo-4-p-tolylbutanoate

Product 1

HCID 86685898Ethyl 5-cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylateYield 115.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 108A (1.2837 g, 4.06 mmol) was dissolved in a mixture of THF (15 mL) and water (3.00 mL) in a 25 mL 1 neck pear shaped flask that was equipped with a magnetic stirrer. Lithium hydroxide monohydrate (0.204 g, 4.87 mmol) was added and the reaction mixture was stirred at rt for 1 h. The reaction mixture was acidified to pH 4 with AcOH, diluted with EtOAc (50 mL) and the solution was washed with water (20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the desired product (1.40 g, 115%) as yellow oil. LCMS Anal. Calc'd for C17H18N2O3 298.1, found [M+H] 299.1.

Workup

  1. customwas equipped with a magnetic stirrer
  2. washthe solution was washed with water (20 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80e00916ceb048edaf66008081cb30b3
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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