(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile synthesis
- Product Name:(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile
- CAS Number:500292-94-4
- Molecular formula:C11H12N2
- Molecular Weight:172.23
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Yield: 73%
Reaction Conditions:
with sodium acetate;palladium diacetate in N,N-dimethyl acetamide at 140;Inert atmosphere;
Steps:
1.1 Step 1: (E) -3- (4-Amino-3,5-dimethylphenyl) acrylonitrile (7)
A solution of sodium acetate (3.2 g, 39 mmol), palladium acetate (0.224 g, 1 mmol), tris (o-methoxy) phosphine (0.608 g,2 mmol) was added to N, N-dimethylacetamide (30 mL) and heated to 140 ° C under nitrogen atmosphere,A solution of 2,6-dimethyl-p-bromoaniline (2 g, 10 mmol) and acrylonitrile (2.12 g, 40 mmol) in N, N-dimethylacetamide was added to the above system and maintained at 140 ° C overnight. The reaction mixture was cooled to room temperature, filtered through celite, extracted with the appropriate amount of water and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and the residue was purified by column chromatography (petroleum ether: 5: 1)To compound 7. Trans-7,1.25 g, 73%.
References:
Luoyang Juhui Pharmaceutical Technology Co., Ltd.;Zhang Hongli;Yang Songfeng CN106749203, 2017, A Location in patent:Paragraph 0137; 0138; 0139; 0140; 0141
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