Formic Acid → HCID 11615419, compound

HRID 1199547Notes

Reaction equation

HRID 1199547 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[NH:11][CH3:12])[C:6]#N.[CH:15](O)=O.[OH2:18]>[Ni]>[CH3:12][N:11]([CH3:15])[C:10]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH:6]=[O:18])=[CH:8][C:9]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 19867132HCID 19867132, compound

Product 1

HCID 11615419HCID 11615419, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 91 g of the 3,5-dimethoxy-4-methylaminobenzonitrile obtained in Example 2, 726 g of formic acid and 29 g of p-formaldehyde are heated to reflux for 1 hour. The mixture is then cooled to 20°-30° C. and treated with 181 ml of water and 91 g of Raney-nickel alloy. The reaction mixture is heated to reflux for 1.5 hours, whereby the reaction starts vigorously at 80° C. The reaction mixture is cooled to 25°-30° C. and filtered in such a manner that the metal is always covered with solvent. The filter cake is washed with formic acid and the solution is evaporated under reduced pressure and thereafter treated with 360 ml of toluene and 360 ml of water. The pH is adjusted to 5.5 to 6 by adding 30% aqueous sodium hydroxide solution. After adding 7 g of active charcoal, the reaction mixture is filtered. The filter cake is washed with toluene and the organic phase is concentrated under reduced pressure. 80 g of 4-dimethylamino-3,5-dimethoxybenzaldehyde are obtained as an oil.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture is then cooled to 20°-30° C.
  4. temperatureThe reaction mixture is heated
  5. temperatureto reflux for 1.5 hours
  6. customstarts vigorously at 80° C
  7. temperatureThe reaction mixture is cooled to 25°-30° C.
  8. filtrationfiltered in such a manner that the metal
  9. washThe filter cake is washed with formic acid
  10. customthe solution is evaporated under reduced pressure
  11. additiontreated with 360 ml of toluene and 360 ml of water
  12. additionby adding 30% aqueous sodium hydroxide solution
  13. additionAfter adding 7 g of active charcoal
  14. filtrationthe reaction mixture is filtered
  15. washThe filter cake is washed with toluene
  16. concentrationthe organic phase is concentrated under reduced pressure

Sources & evidence

ORD record
ord-57674c54348245edad6e370f717f9931
Source dataset
uspto-grants-1990_02
Patent number
US04900859

Reaction notes

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