Benzaldehyde → HCID 21853790, compound

HRID 1580936Notes

Reaction equation

HRID 1580936 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[N:6]=[C:7]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:8]2[C:9](=[O:11])[CH:10]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:16][C:15]1[C:7]2=[N:6][C:5](/[CH:4]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:10][C:9](=[O:11])[N:8]2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5239852,9-Dimethyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 10942334Sodium Methoxide

Product 1

HCID 21853790HCID 21853790, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.1g of sodium methoxide and 25ml of absolute methanol is added 1.1g of 2,9-dimethyl-4H-pyrido-[1,2-a]pyrimidin-4-one, followed by 2.2g of benzaldehyde. The mixture is heated and stirred under reflux for 15 hours and concentrated on a rotary evaporator in vacuo at 45°C. The residual material is distributed between 100ml of chloroform and 50ml of water. The two solutions are separated and the chloroform solution is washed with saturated aqueous sodium chloride, dried, filtered, and the filtrate concentrated. The residual material is recrystallized from 100ml of cyclohexane to yield 0.44g of the title compound, melting point 150°-152°C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 15 hours
  3. concentrationconcentrated on a rotary evaporator in vacuo at 45°C
  4. customThe two solutions are separated
  5. washthe chloroform solution is washed with saturated aqueous sodium chloride
  6. customdried
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customThe residual material is recrystallized from 100ml of cyclohexane

Sources & evidence

ORD record
ord-f4dbf96958de4f6eb56f9447a07cc96a
Source dataset
uspto-grants-1976_01
Patent number
US03935197

Reaction notes

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