Acetic Acid → 3,4-METHYLENEDIOXYBENZYLIDENE ANILINE

HRID 631941Notes

Reaction equation

HRID 631941 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.C(O)C.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>O>[O:11]1[C:3]2[CH:2]=[CH:1][C:6]([CH:7]=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:5][C:4]=2[O:9][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6115AnilineHCID 8438Piperonal

Product 1

HCID 1413733,4-METHYLENEDIOXYBENZYLIDENE ANILINEYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Piperonal (0.63 g, 4.22 mmol), ethanol (4 ml), and aniline (0.38 g, 4.22 mmol) were put in a 25 ml flask, and acetic acid (10 ml) was slowly added dropwise thereto while the mixture was stirred under nitrogen charging conditions, followed by stirring at 80° C. for 12 hours. Then, the temperature of the mixture was lowered to 0° C., followed by the addition of a little water to obtain a solid. The filtering was performed while the solid was washed with cool ethanol, thereby giving clean E)-N-(benz[d][1,3]dioxol-5-ylmethylene)aniline (LJ-2477) with a yield of 45%.

Workup

  1. stirringby stirring at 80° C. for 12 hours
  2. customwas lowered to 0° C.
  3. customto obtain a solid
  4. washwas washed with cool ethanol

Sources & evidence

ORD record
ord-115edcab6dac4df4a3ba19862198ee29
Source dataset
uspto-grants-2016_04
Patent number
US09321751B2

Reaction notes

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