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N-Isopropyl-2-methoxybenzamide synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1: isopropylamine;ortho-anisaldehyde in toluene at 20; for 41 h;
Stage #2: with sodium tetrahydroborate in methanol at 20; for 3 h;
Stage #3: with hydrogenchloride in water;

Steps:

8.1

(1) 2-Methoxybenzaldehyde (2.5 g) and isopropylamine (1.65 ml) were dissolved in toluene (5 ml), anhydrous sodium sulfate (5 g) was added to the solution, and the resulting mixture was stirred at room temperature for 41 hour. The reaction mixture was filtered through Celite, then the filtrate was concentrated under reduced pressure, the resulting residue was dissolved in methanol (25 ml), sodium borohydride (700 mg) was added to the solution under ice cooling, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, concentrated hydrochloric acid (8 ml) was added to the residue, the mixture was washed twice with ethyl acetate, and then the aqueous layer was made alkaline with potassium carbonate, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure to obtain a crude product (3.19 g).

References:

EP2287173,2011,A1 Location in patent:Page/Page column 35