Benzaldehyde → N-Benzyl-2,4-dimethoxyaniline

HRID 1982063Notes

Reaction equation

HRID 1982063 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>O.C(O)C.C(O)(=O)C>[CH2:12]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:3]=1[O:2][CH3:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 176522,4-DimethoxyanilineHCID 4311764Sodium borohydride

Product 1

HCID 563579N-Benzyl-2,4-dimethoxyanilineYield 84.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

Into 150 ml of ethanol, 30.6 g of 2,4-dimethoxyaniline and 21.2 g of benzaldehyde were dissolved, and 2 g of acetic acid was added. The mixture was reacted at a temperature of from 50° to 60° C. for 4 hours. The reaction solution was poured into 500 ml of water and extracted with 300 ml of toluene. The toluene solution was separated by liquid separation, then washed with water and concentrated to dryness. The oily product thereby obtained was dissolved into 150 ml of ethanol, and 11.3 g of sodium boro-hydride was added in 2 hours at a temperature of from 30° to 40° C. and reacted therewith. Further, the mixture was stirred for one hour at a temperature of 40° C. The reaction mixture was poured into 1 liter of water and extracted with 500 ml of toluene. The toluene layer was washed with water, concentrated and purified by distillation under reduced pressure, whereby 40.9 g of N-benzyl-2,4-dimethoxyaniline was obtained. The product was a liquid having a boiling point of from 166° to 168° C./2 mmHg.

Workup

  1. customThe mixture was reacted at a temperature of from 50° to 60° C. for 4 hours
  2. extractionextracted with 300 ml of toluene
  3. customThe toluene solution was separated by liquid separation
  4. washwashed with water
  5. concentrationconcentrated to dryness
  6. customThe oily product thereby obtained
  7. additionwas added in 2 hours at a temperature of from 30° to 40° C.
  8. customreacted
  9. extractionextracted with 500 ml of toluene
  10. washThe toluene layer was washed with water
  11. concentrationconcentrated
  12. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-9e10436b97a640bab1dd4842fb40e4b5
Source dataset
uspto-grants-1986_06
Patent number
US04594601

Reaction notes

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