Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-1-naphthonitrile

HRID 1951398Notes

Reaction equation

HRID 1951398 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1)=O.[CH3:15][C:16](=[O:21])[CH2:17][C:18](=[O:20])[CH3:19].C(O)(=O)C.N1CCCCC1>ClCCl>[C:18]([C:17]([C:16](=[O:21])[CH3:15])=[CH:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 124330094-Formylnaphthalene-1-carbonitrile

Product 1

HCID 596030144-(2-Acetyl-3-oxobut-1-en-1-yl)-1-naphthonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

240 mg (1.33 mmol) of 4-formyl-1-naphthonitrile, 132.6 mg (1.33 mmol) of 2,4-pentanedione, 119.3 mg (1.99 mmol) of acetic acid and 22.6 mg (0.27 mmol) of piperidine are dissolved in 20 ml of dichloromethane and heated under reflux with an inverse water trap overnight. Cooling is followed by washing twice with water, and the organic phase is dried with magnesium sulfate. The solvent is removed in a rotary evaporator and the residue is purified by column chromatography (silica gel, mobile phase: initially dichloromethane, then isohexane/ethyl acetate 3:1). The residue after concentration of the product fractions is crystallized from diethyl ether and dried under high vacuum. 340 mg (97.5% of theory) of the title compound are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. temperatureCooling
  4. washby washing twice with water
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. customThe solvent is removed in a rotary evaporator
  7. customthe residue is purified by column chromatography (silica gel, mobile phase
  8. customThe residue after concentration of the product fractions is crystallized from diethyl ether
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-5158365156f24d47a7465fac54d0aa45
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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