I would like to request the Researchers to let me know any procedures or references to carryout synthesis of Schiff bases of 4-Aminosalicylic acid when treated with different substituted benzaldehydes, which results in good yields and requires simple work-up (high atom efficient other than Ultrasound technique or Microwave)
you could try running the reaction in water using catalytic amount of amphiphile like PTS (created by Prof Lipshutz)
@ Greg Petruncio ; thanks for the suggestion, but whether should i go with stirring at room temperature or reflux....?
PTS is an amphiphile used in cross coupling reactions which are totally different from you are doing so you are going to have to experiment and try both. There are other amphiphile out there that might be worth trying too.
My guess is since your amine is aromatic it is not as nucleophilic as aliphatic primary amine so you will probably have to heat.
I did a similar reaction with analine derivatives on benzophenone. Used toluene with a bidwell-sterling type water trap and small amount of acid catalyst. If you run into problems, esterify it in methanol and try these conditions; it will be high yielding and likely easy to recrystallize.
@ Daniel Austin ; thank you for sharing your experience, I will plan for a trial using toluene.
Hi, you could try using ultrasonic irradiation, the reaction time is lower than room temperature (15 minutes) and are not observed secondary products as reflux
I would suggest a dean-stark in toluene with a catalytic amount of pTSA.
I recommend using CH2Cl2 ir CHCl3 or toluene in the presence of catalytic amount of acid to facilitate the process. In addition, add Molecular Sieves (3 or 4A) or use DST to remove the water.
Try Solvent and catalyst free synthesis
This method works without solvent and catalyst The reaction mixture is grindedin a mortar with a pestle and progress of the reaction is monitored by column chromatography and TLC .Literature reports reveal that such reactions complete within 2-3 minute.
K.A.Shaikh, V.A.Patil, A.M.Zamir ‘‘Solid phase promoted greener synthesis andantibacterial activity of novel Schiff base under catalytically free condition’’ Elixir Org. Chem., 43, 6960-6963(2012
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