Methanol → 2-Oxo-4,6-dipropyl-1,2-dihydropyridine-3-carbonitrile

HRID 544550

Reaction equation

HRID 544550 reaction equation
[CH3:1][CH2:2][CH2:3][C:4](=O)[CH2:5][C:6](=O)[CH2:7][CH2:8][CH3:9].CO.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].C[O-].[Na+]>O.C(O)(=O)C>[C:14]([C:16]1[C:17](=[O:18])[NH:19][C:6]([CH2:7][CH2:8][CH3:9])=[CH:5][C:4]=1[CH2:3][CH2:2][CH3:1])#[N:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 7898CyanoacetamideHCID 264544,6-NonanedioneHCID 10942334Sodium Methoxide

Product 1

HCID 132990072-Oxo-4,6-dipropyl-1,2-dihydropyridine-3-carbonitrileYield 81.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-Cyano-4,6-di-n-propyl-2(1H)-pyridinone was prepared as follows: A mixture containing 15.6 g of 4,6-nonanedione, 200 ml of methanol, 10 g of cyanoacetamide and 6 g of sodium methoxide was refluxed with stirring for 22 hours and then stripped to dryness in vacuo. The residue was dissolved in 100 ml of water and the solution acidified with acetic acid. The white precipitate was collected, washed with water, air-dried, recrystallized from isopropyl alcohol-n-hexane and dried in vacuo at 80°-85° C. to produce 16.7 g of 3-cyano-4,6-di-n-propyl-2(1H)-pyridinone, m.p. 151°-152° C.

Workup

  1. custom3-Cyano-4,6-di-n-propyl-2(1H)-pyridinone was prepared
  2. temperaturewas refluxed
  3. customThe white precipitate was collected
  4. washwashed with water
  5. customair-dried
  6. customrecrystallized from isopropyl alcohol-n-hexane
  7. customdried in vacuo at 80°-85° C.

Sources & evidence

ORD record
ord-df17b0cc4947456784a3aa58265e2ed9
Source dataset
uspto-grants-1984_05
Patent number
US04451469

Linked notes

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