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

HRID 259380Notes

Reaction equation

HRID 259380 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), methylcello-solve (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--HCl (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
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-d786c996b26840b6a7aeeb62ddc1c96d
Source dataset
uspto-grants-1977_07
Patent number
US04038065

Reaction notes

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