3-Pyridinecarboxaldehyde → HCID 18467015, compound

HRID 2229233Notes

Reaction equation

HRID 2229233 reaction equation
C[O-].[Na+].[CH:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][CH:6]=1.[C:12]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:14])[CH3:13]>CO>[N:7]1[CH:8]=[CH:9][CH:10]=[C:5](/[CH:4]=[CH:13]/[C:12]([C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=2)=[O:14])[CH:6]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 698856-AcetyltetralinHCID 10942334Sodium Methoxide

Product 1

HCID 18467015HCID 18467015, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 28% solution of sodium methoxide in MeOH (0.9 g) was added to a mixture of nicotinaldehyde (6.71 g) and 6-acetyltetraline (10.83 g) in MeOH (50 ml) and the mixture was stirred at room temperature for 12 hours. After removal of the solvent, the residue was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (hexane-ethyl acetate =1:1) followed by recrystallization from hexane-ethyl acetate to give the titled compound (9.30 g).

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (hexane-ethyl acetate =1:1)
  7. customfollowed by recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4fbab8bddcac4c7cb2c9c0ae9c0fed62
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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