Hydrochloric Acid → Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

HRID 593870

Reaction equation

HRID 593870 reaction equation
C(O[C:4]([CH3:13])=[CH:5][C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])C.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[C:14]([C:16]1[C:17](=[O:18])[NH:19][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[CH3:13])#[N:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 275522CID 275522

Product 1

HCID 275523Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylateYield 65.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of ethyl 4-ethoxy-2-oxopent-3-enoate (22.5 g, 121 mmol) and 2-cyanoacetamide (9.0 g, 107 mmol) in acetone (250 mL) was added potassium carbonate (15.8 g, 114 mmol). The reaction was refluxed (85° C. oil bath) for 10 hr (the reaction formed a thick ppt. in a deep red solution). The slurry was added to cold 1N HCl (230 mL) in ice. After stirring for 30 min. the suspension was filtered, washed with water and dried under vacuum to give the product ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (14.51 g, 70.4 mmol, 65.7% yield) as a light pink solid. 1H NMR (400 MHz, DMSO-d6) δ12.60 (br. s., 1H), 7.05 (br. s., 1H), 4.34 (q, J=7.1 Hz, 2H), 2.45 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). MS(ES)+ m/e 206.8 [M+H]+.

Workup

  1. customformed a thick ppt
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-952798e87ea34fe590227fa907cd7ca1
Source dataset
uspto-grants-2016_01
Patent number
US09242962B2

Linked notes

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