(2-CHLORO-4-NITROPHENYL)-ACETONITRILE synthesis
- Product Name:(2-CHLORO-4-NITROPHENYL)-ACETONITRILE
- CAS Number:89277-99-6
- Molecular formula:C8H5ClN2O2
- Molecular Weight:196.59
Yield:-
Reaction Conditions:
Stage #1: ethyl 2-cyanoacetatewith potassium hydroxide in dimethyl sulfoxide; for 1 h;
Stage #2: 3-chloro-4-fluoronitrobenzene in dimethyl sulfoxide at 20; for 7.5 h;
Stage #3: with 4-ethynylbenzenesulfonamide;acetic acid in water; for 3 h;Heating / reflux;
Steps:
57b
Example 57b; (2-Chloro-4-nitro-phenyl)-acetonitrile; 2.94 g (26 mmol) of ethyl cyanoacetate (Fluka, Buchs, CH) and 1.66 g (26 mmol) of KOH in 8 mi of DMSO are stirred for 1 h, then 3.51 g (20 mmol) of 2-chloro-1-fluoro-4-nitro- benzene (Aldrich, Buchs, CH) are added and the reaction mixture is stirred for 7.5 h at RT. A solution of 37% aqueous HCI and 5.6 ml of acetic acid is added and the reaction mixture is heated for 3 h at reflux, then quenched with H20 and extracted with diethylether (2x). The combined organic layers are washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 10: 1 to 6: 1) to give the title compound as a gel solid : ES-MS: 195 (M-H)- ; analytical HPLC: tret= 4. 01 minutes (Grad 1).
References:
WO2005/54238,2005,A1 Location in patent:Page/Page column 83-84
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