3-(3-DIMETHYLAMINO-PHENYL)-3-OXO-PROPIONITRILE synthesis
- Product Name:3-(3-DIMETHYLAMINO-PHENYL)-3-OXO-PROPIONITRILE
- CAS Number:887591-49-3
- Molecular formula:C11H12N2O
- Molecular Weight:188.23
16518-64-2
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Yield:887591-49-3 57 %
Reaction Conditions:
Stage #1: acetonitrilewith sodium hydride in toluene;mineral oil at 0 - 50;Inert atmosphere;
Stage #2: 3-(dimethylamino)benzoic acid methyl ester in toluene;mineral oil at 110;Inert atmosphere;
Steps:
Step 1 - 3-(3-(Dimethylamino)phenyl)-3-oxopropanenitrile.
To a solution of ACN (6 mL) in toluene (20 mL) was added NaH (1.34 g, 33.48 mmol, 60% dispersion in mineral oil) at 0 °C, then the mixture was stirred at 50 °C for 2 h. Next, methyl 3-(dimethylamino)benzoate (2 g, 11.16 mmol, CAS 16518-64-2) in toluene (20 mL) was added and the mixture was stirred at 110 °C for 4 hours. On completion, the residue was diluted with water (100 mL) and extracted with ethyl acetate (80 mL). The combined organic layers were washed with brine (40 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=4/1) to give a title compound (1.2 g, 57% yield) as a yellow solid. LC/MS (ESI, m/z): [M +1]+ = 189.1+.
References:
WO2022/178532,2022,A1 Location in patent:Paragraph 00793; 00859; 00860
