2-Hydroxy-4-Methoxybenzaldehyde → 3-Nicotinoyl-7-methoxycoumarin

HRID 25876

Reaction equation

HRID 25876 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O[C:16]1C=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1C=O>N1CCCCC1>[C:1]([C:9]1[C:10](=[O:11])[O:12][C:13]2[C:17]([CH:16]=1)=[CH:20][CH:21]=[C:22]([O:24][CH3:25])[CH:14]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 222197Ethyl 3-oxo-3-(pyridin-3-yl)propanoate

Product 1

HCID 212173313-Nicotinoyl-7-methoxycoumarin

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

A mixture of 0.65 g ethyl nicotinoylacetate, 0.5 g 2-hydroxyanisaldehyde and 10 ml alcohol was heated on a steam bath until solution was attained. Five drops of piperdine were added and heating was continued. After several minutes the reaction mixture solidified. An additional 10 ml of alcohol were added and the reaction mixture heated another 15 minutes. After cooling, the solid was collected and recrystallized twice from a mixture of alcohol and acetonitrile.

Workup

  1. temperaturewas heated on a steam bath until solution
  2. temperatureheating
  3. waitAfter several minutes the reaction mixture solidified
  4. temperaturethe reaction mixture heated another 15 minutes
  5. temperatureAfter cooling
  6. customthe solid was collected
  7. customrecrystallized twice from a mixture of alcohol and acetonitrile

Sources & evidence

ORD record
ord-0df72b8e35584857b395332273362433
Source dataset
uspto-grants-1979_04
Patent number
US04147552

Linked notes

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