Benzoic Acid → HCID 67267624, compound

HRID 250207

Reaction equation

HRID 250207 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:14][O:13][C:11](=[O:12])[C:10](=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 2733872tert-Butyl methyl malonate

Product 1

HCID 67267624HCID 67267624, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of pyridine-3-carboxaldehyde (2.72 g), propanedioic acid, 1,1-dimethylethyl methyl ester (4.42 g), piperidine (0.173 g) and benzoic acid (0.155 g) in benzene (100 ml) was heated at reflux with removal of water to a Dean-Stark trap for 12 hours. The cooled mixture was washed with bicarbonate solution, concentrated under vacuum and the residue was purified by column chromatography, eluting with ethyl acetate-hexane (3:7) to afford racemic 2-pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester as an oil (3.21 g).

Workup

  1. temperaturewas heated
  2. washThe cooled mixture was washed with bicarbonate solution
  3. concentrationconcentrated under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting with ethyl acetate-hexane (3:7)

Sources & evidence

ORD record
ord-339ee568794649a79418bafe7076f999
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Linked notes

Loading…