Octane → 1-(2-Ethylhexyl)-3-cyano-6-methylpyrid-2-one

HRID 2419967

Reaction equation

HRID 2419967 reaction equation
[CH2:1]([CH:3]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:4][NH:5][C:6](=[O:10])[CH2:7][C:8]#[N:9])[CH3:2].CO[CH:17]=[CH:18][C:19](=O)[CH3:20].COCCO.CCCCCCCC>C(Cl)Cl>[CH2:1]([CH:3]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:4][N:5]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:7]([C:8]#[N:9])[C:6]1=[O:10])[CH3:2]

Participants

6

Reactant 4

HCID 356OctaneHCID 80192-MethoxyethanolHCID 942973-Buten-2-one, 4-methoxy-2×HCID 45907042-cyano-N-(2-ethylhexyl)acetamide

Product 1

HCID 203121811-(2-Ethylhexyl)-3-cyano-6-methylpyrid-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-ethylhexyl) cyanoacetamide (60.4 g., 0.30 mole), 4-methoxy-3-butene-2-one (60.0 g., 0.60 mole), methylcellosolve (250 ml.) and 1,4-diazobicyclo [2.2.2.] octane (6.0 g.) are heated at reflux for 4 hours. Additional 4-methoxy-3-butene-2-one(30 g.) is added and reflux is continued for another 2 hours. The solvent is removed in vacuo to give an oil. The oil is dissolved in methylene chloride and extracted first with 2N-HC (150 ml.) and then with water (2 × 250 ml.). The organic layer is dried over sodium sulfate, filtered and evaporated to dryness to give a 90% yield of crude product which is characterized by nmr and ir analysis.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturereflux
  3. customThe solvent is removed in vacuo
  4. customto give an oil
  5. extractionextracted first with 2N-HC (150 ml.)
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-3ff1fb0d64c245e192132ff20b39bc52
Source dataset
uspto-grants-1978_08
Patent number
US04108630

Linked notes

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