Nitrogen → 6-Ethyl-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 42471Notes

Reaction equation

HRID 42471 reaction equation
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][C:14](=O)/[CH:15]=[CH:16]/[CH2:17][CH3:18].N#N.O=O>CC#N.Cl>[CH2:14]([C:15]1[NH:12][C:10](=[O:11])[C:9]([C:7]#[N:8])=[C:17]([CH3:18])[CH:16]=1)[CH3:13]

Participants

8

Reactant 5

HCID 947NitrogenHCID 977OxygenHCID 7898CyanoacetamideHCID 53677443-Hexen-2-oneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 106308306-Ethyl-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 21%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of t-BuOK (17.2 g, 153 mmol) and cyanoacetamide (13 g, 153 mmol) in CH3CN (225 mL) was added (3E)-3-hexen-2-one (15 g, 153 mmol) at room temperature under N2 atmosphere. The reaction mixture was stirred for 30 min. To the reaction mixture was added additional t-BuOK (51.4 g), and the N2 was displaced by oxygen. After stirring for 1 h without external cooling, the mixture was diluted with 4 N HCl, which was added slowly and with good stirring. The mixture was filtered, washed with EtOH, dried to give 6-ethyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (5 g, 21%). 1H NMR (400 MHz, DMSO-d6) δ 12.33 (br. s., 1H), 6.18 (s, 1H), 2.45 (q, 2H), 2.30 (s, 3H), 1.11 (t, 3H).

Workup

  1. stirringAfter stirring for 1 h without external cooling
  2. additionwas added slowly and with good stirring
  3. filtrationThe mixture was filtered
  4. washwashed with EtOH
  5. customdried

Sources & evidence

ORD record
ord-4675cdc5d7b549e5aee45f4612babffe
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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