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To a heterogeneous solution of 3,5-diamino benzoic acid (0.23 g, 1.50 mmol) in MeOH(2 mL) was added a solution of aldehyde 7 (1.00 g, 3.15 mmol) in MeOH (20 mL). Afterstirring at room temperature for 20 min, the reaction flask was cooled in an ice bath and NaBH4 (0.096 g, 2.53 mmol) was added. The reaction was allowed to stir at room temperature overnight, after which TLC in 5% MeOH, 1% Et3N in CH2Cl2 confirmed its completion. The reaction was cooled to 0 C and distilled H2O (5 mL) was added. The DMSO, SO3.pyr,DIPEA, solution was neutralized with 2N HCl (6.4 mL) and extracted with CH2Cl2 (3X, 30 mL). The organic layers were combined and dried over MgSO4 and rotary evaporated to afford a green foam. The crude product was purified by silica gel column in 5% MeOH and 1% Et3N in CH2Cl2 to afford 0.98 g (92%) of a gold foam product.
3,5-bis[(E)-2-hydroxy-3,5-diiodobenzylidene]amino}benzoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
97%
In methanol; for 3h;Reflux;
General procedure: Imines 2a-2h, 3a-3h, 4a-4h, 5a-5h, and 6a-6h were synthesized according to Krtk etal.(2020). Briefly, 1 mmol of amino compound (2, 4, 5, 6) was dissolved in 7 ml of MeOH and then appropriate aldehyde (1.1 mmol) was added in one portion. In the case of imines 3a-3h, 3,5-diaminobenzoic acid 3 (1 mmol) was dissolved in 10 ml of MeOH and 2.2 mmol of appropriate aldehyde was added. The reaction mixture was refluxed for 3 hours. After additional 12 hours of stirring at room temperature, the reaction mixture was stored at -20C for 1 h. The precipitate formed was filtered off and washed successively by MeOH and diethyl ether thoroughly. If necessary, the products were crystallized from tetrahydrofuran/MeOH to obtain pure Schiff bases.
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