2-Acetylnaphthalene → HCID 14434140, compound

HRID 2229229Notes

Reaction equation

HRID 2229229 reaction equation
C[O-].[Na+].[CH:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][CH:6]=1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22]([CH3:24])=[O:23].S([O-])([O-])(=O)=O.[Na+].[Na+]>CO.C(OCC)(=O)C>[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22](/[CH:24]=[CH:4]/[C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:23]

Participants

7

Reactant 4

HCID 71222-AcetylnaphthaleneHCID 103713-PyridinecarboxaldehydeHCID 24436Sodium SulfateHCID 10942334Sodium Methoxide

Product 1

HCID 14434140HCID 14434140, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 28% solution of sodium methoxide in MeOH (0.90 g) was added to a stirred mixture of nicotinaldehyde (9.70 g) and methyl 2-naphthyl ketone (15.26 g) in MeOH (150 ml). Sodium sulfate (10 g) was added to the mixture and the mixture was stirred for 30 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was recrystallized from cold MeOH to give the titled compound (10.68 g).

Workup

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from cold MeOH

Sources & evidence

ORD record
ord-06e3691b28a54f6b80415a5dc382cd2f
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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