Acetic Acid → HCID 23295350, compound

HRID 1955376Notes

Reaction equation

HRID 1955376 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[C:10]([OH:13])(=O)[CH3:11].[CH3:14][C:15]([CH3:17])=O>O>[CH:15]([NH:1][C:2]1[CH:3]=[CH:6][C:11]([CH:10]=[O:13])=[C:8]([CH3:7])[CH:9]=1)([CH3:17])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 180AcetoneHCID 682552-Aminobenzaldehyde

Product 1

HCID 23295350HCID 23295350, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500-ml flask, place 46.05 g (0.2 m) of the blocked aminobenzaldehyde, 125 ml of acetic acid and 23.23 g (0.4 m) of acetone. Heat the mixture to 30 C. Add 11.78 g (0.2 m) of borane-dimethylamine complex slowly keeping the temperature below 50 C. Stir the mixture at 50 C. for 1 hour, and cool to room temperature. Add 200 ml of water and stir for 15 minutes. Collect solids, wash with water, and deliquor as much as possible. In a 500-ml flask, place the wet intermediate, 100 ml of methanol, and 60 g of 50% NaOH solution. Heat the mixture under reflux for 1 hour. Add 120 ml of hot water and distill off methanol till approximately 120 ml of distillate is collected and pot temperature reaches close to 100 C. Heat the mixture under reflux for 1 hour, and then cool to room temperature. Add 150 ml of propyl acetate, stir for 5 minutes, and let layers settle. Separate bottom water layer. Wash the propyl acetate solution with 100 ml of brine. Dry over magnesium sulfate and distill propyl acetate under a reduced pressure to a red viscous oil. Add 150 ml of heptanes with vigorous stirring. Stir the resulting slurry at room temperature for 45 minutes. Collect product, wash with heptanes, and dry to give 28.35 g (80%) of 4-isopropylamino-2-methylbenzaldehyde as yellow solids.

Workup

  1. temperatureHeat the mixture to 30 C
  2. additionAdd 11.78 g (0.2 m) of borane-dimethylamine complex
  3. stirringstir for 15 minutes
  4. customCollect solids
  5. washwash with water, and deliquor as much as possible
  6. temperatureHeat the mixture
  7. temperatureunder reflux for 1 hour
  8. additionAdd 120 ml of hot water
  9. distillationdistill off methanol till approximately 120 ml of distillate
  10. customis collected
  11. custompot temperature reaches close to 100 C
  12. temperatureHeat the mixture
  13. temperatureunder reflux for 1 hour
  14. temperaturecool to room temperature
  15. additionAdd 150 ml of propyl acetate
  16. stirringstir for 5 minutes
  17. customSeparate bottom water layer
  18. washWash the propyl acetate solution with 100 ml of brine
  19. dry with materialDry over magnesium sulfate
  20. distillationdistill propyl acetate under a reduced pressure to a red viscous oil
  21. additionAdd 150 ml of heptanes with vigorous stirring
  22. stirringStir the resulting slurry at room temperature for 45 minutes
  23. washCollect product, wash with heptanes
  24. customdry

Sources & evidence

ORD record
ord-cb0ee59683db4130bb24d4a8118cc4df
Source dataset
uspto-grants-2000_09
Patent number
US06124503

Reaction notes

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